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Journal articles on the topic 'Alcohol synthesis; Organometallics'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Narayanaperumal, Senthil, Ricardo S. Schwab, Wystan K. O. Teixeira, and Danilo Yano de Albuquerque. "Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds." Synthesis 52, no. 13 (March 16, 2020): 1855–73. http://dx.doi.org/10.1055/s-0039-1690847.

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Enantiomerically enriched diaryl, aryl heteroaryl, and diheteroaryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

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2

Chan, T. H., C. J. Li, M. C. Lee, and Z. Y. Wei. "1993 R.U. Lemieux Award Lecture Organometallic-type reactions in aqueous media—a new challenge in organic synthesis." Canadian Journal of Chemistry 72, no. 5 (May 1, 1994): 1181–92. http://dx.doi.org/10.1139/v94-151.

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The development of organometallic-type reactions in aqueous media is reviewed. Coupling reactions of allyl halides with carbonyl compounds mediated by zinc, or tin, or indium in aqueous media to give homoallylic alcohols are discussed. The stereochemical outcome is compared with similar reactions in organic solvents. A concise synthesis of (+)-muscarine is used to illustrate the usefulness of aqueous organometallic-type reactions in organic synthesis. The procedure to protect–deprotect hydroxy functional groups may not be necessary in these reactions. An application in the carbohydrate area is demonstrated with the synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). The mechanistic possibilities of organometallic-type reactions in aqueous media are outlined.

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3

Shu, Xing-Zhong, Feng-Feng Pan, Peng Guo, and Xiaochuang Huang. "Synthesis of Dibenzyls by Nickel-Catalyzed Homocoupling of Benzyl Alcohols." Synthesis 53, no. 17 (March 25, 2021): 3094–100. http://dx.doi.org/10.1055/a-1467-2432.

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AbstractDibenzyls are essential building blocks that are widely used in organic synthesis, and they are typically prepared by the homocoupling of halides, organometallics, and ethers. Herein, we report an approach to this class of compounds using alcohols, which are more stable and readily available. The reaction proceeds via nickel-catalyzed and dimethyl oxalate assisted dynamic kinetic homocoupling of benzyl alcohols. Both primary and secondary alcohols are tolerated.

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4

Elorriaga, David, María Jesús Rodríguez-Álvarez, Nicolás Ríos-Lombardía, Francisco Morís, Alejandro Presa Soto, Javier González-Sabín, Eva Hevia, and Joaquín García-Álvarez. "Combination of organocatalytic oxidation of alcohols and organolithium chemistry (RLi) in aqueous media, at room temperature and under aerobic conditions." Chemical Communications 56, no. 63 (2020): 8932–35. http://dx.doi.org/10.1039/d0cc03768k.

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5

Nicholas, Kenneth M., and Chandrasekhar Bandari. "Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides." Synthesis 53, no. 02 (October 7, 2020): 267–78. http://dx.doi.org/10.1055/s-0040-1707269.

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AbstractThe prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amounts of low-valent transition-metal reagents to form the corresponding hydrocarbon dimers. More recently, the use of redox-active transition-metal catalysts together with a reductant has enhanced the practical applications and scope of the reductive coupling of alcohols. Inclusion of other reaction partners with alcohols such as unsaturated hydrocarbons and main-group organometallics has further expanded the diversity of carbon skeletons accessible and the potential for applications in chemical synthesis. Catalytic reductive coupling and cross-coupling reactions of epoxides are also highlighted. Mechanistic insights into the means of C–O activation and C–C bond formation, where available, are also highlighted.1 Introduction2 Stoichiometric Reductive Coupling of Alcohols3 Catalytic Reductive Coupling of Alcohols3.1 Heterogeneous Catalysis3.2 Homogeneous Catalysis4 Reductive Cross-Coupling of Alcohols4.1 Reductive Alkylation4.2 Reductive Addition to Olefins5 Epoxide Reductive Coupling Reactions6 Conclusions and Future Directions

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6

Cicco, Luciana, María J. Rodríguez-Álvarez, Filippo M. Perna, Joaquín García-Álvarez, and Vito Capriati. "One-pot sustainable synthesis of tertiary alcohols by combining ruthenium-catalysed isomerisation of allylic alcohols and chemoselective addition of polar organometallic reagents in deep eutectic solvents." Green Chemistry 19, no. 13 (2017): 3069–77. http://dx.doi.org/10.1039/c7gc00458c.

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7

Vizer, S. A., and K. B. Yerzhanov. "Heterocycles Synthesis at Carbonylation of Acetylenic Compounds." Eurasian Chemico-Technological Journal 5, no. 2 (April 5, 2016): 145. http://dx.doi.org/10.18321/ectj294.

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The carbonylation of unsaturated hydrocarbons, alcohols, organic halides and other substrates catalyzed by transition metals, salts of transition metals and organometallic complexes is a wide used synthesis method of new carbonyl, carboxyl and alkoxy carbonyl containing compounds including creation or modificationt of heterocycles. The data about synthesis of heterocycles at carbonylation of acetylenic compounds have been appeared at last 20 years and are demonstrated in our review. Introduction of carbon monoxide in the catalytic reactions of acetylenic compounds permits to obtain in oneput process the diverse heterocycles, having carbonyl, carboxyl or alkoxycarbonyl substitutes or containing these fragments inside of heterocycles.

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8

Gheorghievici, Gavril Lucian, Corneliu Trisca Rusu, Elena Voicila, Ion Marius Nafliu, Anca Maria Cimbru, and Szidonia Katalin Tanczos. "Titanium Dioxide for Biomedical Uses I. The controlled production of nanoparticles by hidrothermal synthesis moderated by dimedone." Revista de Chimie 68, no. 1 (February 15, 2017): 11–15. http://dx.doi.org/10.37358/rc.17.1.5378.

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The controlled the solvo-hydro-thermal titanium dioxide synthesis moderated by dimedone from organometallic precursors is approached in order to obtain nanoparticles compatible with the polymeric systems used in the dental technique. The experiments carried out with relation to the production of titanium dioxide nanoparticles using the solvo-hydro-thermal synthesis allowed the production of three types of materials by means of varying the nature of the used solvent: methanol, ethanol and propanol (TiO2-M, TiO2-E and TiO2-P).The characterisation using electron microscopy (SEM and HRTEM), X-ray analysis, FTIR and UV-Vis spectrometry show that the diameter of the produced nanoparticles is less than 15 nm and decreases in the order: dpMethanol ] dpEthanol ] dpPropanol. The nanoparticles contain trace organic substances which the smaller they are, the bigger the alcohol chain used as a solvent is. The adsorption of a target dye showed increasing values with the increasing number of atoms in the hydrocarbon alcohol chain. The highlighted characteristics suggest the possibility of using the synthesised nanoparticles in the production of hard implants for dental reconstruction.

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9

Loughrey, Bradley T., Michael L. Williams, Thomas J. Carruthers, Peter G. Parsons, and Peter C. Healy. "Synthesis, Structure, and Selective Cytotoxicity of Organometallic Cp*RuII O-Alkyl-N-phenylcarbamate Sandwich Complexes." Australian Journal of Chemistry 63, no. 2 (2010): 245. http://dx.doi.org/10.1071/ch09420.

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Tetraphenylborate salts of the η6-arene Cp*RuII O-alkyl-N-phenyl carbamate organometallic sandwich complexes, [Cp*Ru(PhNHCO2R)]BPh4 for R = Me (1), Et (2), and n-Pr (3), have been prepared by a facile one-pot reaction between ruthenium trichloride, pentamethylcyclopentadiene, and phenylisocyanate in refluxing alcohol solutions, and have been characterized by Fourier-transform IR and NMR spectroscopy, electrospray mass spectrometry, and single-crystal X-ray structure determinations. In vitro cytotoxicity studies show the complexes to be potent growth inhibitors for a range of tumour cell lines, while expressing significantly lower levels of toxicity towards a normal human fibroblast cell line.

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10

Larock, Richard C., and Sandra K. Stolz-Dunn. "Synthesis of Homoallylic Alcohols via Organometallic Ring Opening of Vinylic Oxetanes." Synlett 1990, no. 06 (1990): 341–43. http://dx.doi.org/10.1055/s-1990-21086.

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11

Geurts, Koen, Stephen P. Fletcher, Anthoni W. van Zijl, Adriaan J. Minnaard, and Ben L. Feringa. "Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 1025–37. http://dx.doi.org/10.1351/pac200880051025.

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Asymmetric allylic alkylations (AAAs) are among the most powerful C-C bond-forming reactions. We present a brief overview of copper-catalyzed AAAs with organometallic reagents and discuss our own contributions to this field. Work with zinc reagents and phosphoramidite ligands provided a framework for later developments which employ Grignard reagents and ferrocenyl ligands. High yields and excellent regioselectivities and enantioselectivities are achieved. The AAAs may be more general than previously envisioned, in terms of using substrates functionalized with heteroatoms at various positions; heteroatom substituents at the γ-position provide densely functionalized building blocks. These h-AAA reactions rely on the design of appropriate substrates containing heteroatoms and have allowed us to demonstrate viable new approaches toward the synthesis of versatile organic building blocks. We illustrate that the chiral secondary allylic alcohols, primary homo-allylic alcohols and amines can readily be obtained in high enantiomeric purity in a catalytic asymmetric fashion by copper-catalyzed AAAs. Furthermore, we show that manipulation of the terminal olefin provides chiral building blocks where the ee of the starting materials is preserved.

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12

Grymel, Aleksander, Piotr Latos, Karolina Matuszek, Karol Erfurt, Natalia Barteczko, Ewa Pankalla, and Anna Chrobok. "Sustainable Method for the Synthesis of Alternative Bis(2-Ethylhexyl) Terephthalate Plasticizer in the Presence of Protic Ionic Liquids." Catalysts 10, no. 4 (April 23, 2020): 457. http://dx.doi.org/10.3390/catal10040457.

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Inexpensive Brønsted acidic ionic liquids based on trimethylamine and sulfuric acid are proposed as both solvents and catalysts in the synthesis of alternative plasticizer bis(2-ethylhexyl) terephthalate, which has a broad spectrum of applications in plasticization processes. The utilization of 50 mol % of Brønsted ionic liquid led to the full conversion of terephthalic acid after 8 h of reaction at 120 °C. Additionally, a 100% selectivity of bis(2-ethylhexyl) terephthalate was obtained. The advantage of the presented reaction system is based on the formation of a biphasic system during the reaction. The bottom phase consists of an ionic liquid and water, and the upper phase is created by the ester and unreacted alcohol. This phenomenon helps overcome the equilibrium of the reaction and drives it towards a high yield of product. The presented new approach is proposed as a safe, cost-effective, and alternative method to conventional processes with organometallic compounds that, in turn, leads to greener and a more economically viable technology.

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13

Seshadri, Hemalatha, and Carl J. Lovely. "Application of Olefin Cross-Metathesis to Organometallics. Synthesis of Unsaturated Ferrocenyl Alcohols and Ketones." Organic Letters 2, no. 3 (February 2000): 327–30. http://dx.doi.org/10.1021/ol991282e.

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14

Pelzer, K., O. Vidoni, K. Philippot, B. Chaudret, and V. Collière. "Organometallic Synthesis of Size-Controlled Polycrystalline Ruthenium Nanoparticles in the Presence of Alcohols." Advanced Functional Materials 13, no. 2 (February 5, 2003): 118–26. http://dx.doi.org/10.1002/adfm.200390017.

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15

Chinkov, Nicka, G. Sklute, Helena Chechik, Adi Abramovitch, Deborah Amsallem, J. Varghese, Swapan Majumdar, and I. Marek. "New regio-, stereo-, diastereo- and enantioselective one-pot reactions mediated by organometallic derivatives." Pure and Applied Chemistry 76, no. 3 (January 1, 2004): 517–35. http://dx.doi.org/10.1351/pac200476030517.

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In the first part of the lecture, we will discuss the one-pot preparation of chiral homoallylic alcohol and amine derivatives by a copper-catalyzed four-component reaction. In this process, three new carbon-carbon bonds as well as a quaternary and a tertiary chiral center are created with excellent regio- and diastereoselectivities. When the reaction was performed without adding external electrophiles, a β-elimination reaction took place to give polysubstituted allenes in good overall yields. This strategy of zinc-homologation followed by a β-elimination reaction was also synthetically used for the transformation of sp3 sulfoxides into olefins with potential application in asymmetric synthesis. Finally, in the second part of this lecture, the stereoselective preparation of metallated dienes in only two chemical steps from commercially available products will be described. This new strategy is based on a tandem allylic C-H bond activation of a remote ω-double bond followed by an elimination reaction.

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16

Faigl, Ferenc, Béla Mátravölgyi, Szilvia Deák, Zsuzsanna Erdélyi, Tamás Hergert, and Péter Ábrányi-Balogh. "Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions." Synlett 29, no. 16 (July 25, 2018): 2171–75. http://dx.doi.org/10.1055/s-0037-1610551.

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Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantioselective addition of diethylzinc to benzaldehyde are reported. Systematic modification of the electronic and steric properties of the functional groups resulted in highly efficient catalyst ligands in both series. Quantum-chemical calculations agreed well with the experimental results of this first systematic comparative study on regioisomeric atropisomeric ligands.

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17

Ishihara, Kazuaki, and Manabu Hatano. "Recent Progress in the Catalytic Synthesis of Tertiary Alcohols from Ketones with Organometallic Reagents." Synthesis 2008, no. 11 (June 2008): 1647–75. http://dx.doi.org/10.1055/s-2008-1067046.

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18

Baltazar, Mikael John A., Roy Kristian C. Yanela, Armando, Jr, M. Guidote, and Noriyuki Suzuki. "Palladium-Catalyzed Carbonyl Allylation Reactions Using Tin Chloride: A Mini-Review." KIMIKA 29, no. 1 (August 4, 2018): 22–40. http://dx.doi.org/10.26534/kimika.v29i1.22-40.

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The treatment of allylic alcohols as synthons of carbanions for carbonyl allylation reactions in the presence of a Pd-SnCl2 system has been one of the most interesting and most useful developments demonstrated by Yoshiro Masuyama and co-workers in the field of organic synthesis. The reaction makes use of palladium as an effective catalyst and tin (II) chloride as a low-valent reducing agent which also effectively transforms the allylic group to a nucleophilic group. The organic, as well as organometallic, chemistry of how the transformations occur and how the metals take part in the reaction is of great interest. These could help allow for better optimization of reagents and solvents, for better control of the extent of reaction or yield of desired product, and for possible applications in other reaction systems. This review will focus primarily on the work of Yoshiro Masuyama and various co-workers on carbonyl allylation reactions making use of a Pd-SnCl2 system or substitutes thereof.

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19

Malkov, Andrei V., and Aleksandr E. Rubtsov. "Developing a Methodology for Catalytic Asymmetric Crotylation of Aldehydes." Synlett 32, no. 14 (January 18, 2021): 1397–405. http://dx.doi.org/10.1055/s-0040-1706659.

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AbstractAsymmetric crotylation has firmly earned a place among the set of valuable synthetic tools for stereoselective construction of carbon skeletons. For a long time the field was heavily dominated by reagents bearing stoichiometric chiral auxiliaries, but now catalytic methods are gradually taking center stage, and the area continues to develop rapidly. This account focuses primarily on preformed organometallic reagents based on silicon and, to some extent, boron. It narrates our endeavors to design new and efficient chiral Lewis base catalysts for the asymmetric addition of crotyl(trichloro)silanes to aldehydes. It also covers the development of a novel protocol for kinetic resolution of racemic secondary allylboronates to give enantio- and diastereomerically enriched linear homoallylic alcohols. As a separate topic, cross-crotylation of aldehydes by using enantiopure branched homoallylic alcohols as a source of crotyl groups is discussed. Finally, the synthetic credentials of the developed methodology are illustrated by total syntheses of marine natural products, in which crotylation plays a key role in setting up stereogenic centers.1 Introduction2 Pyridine N-Oxides as Lewis Base Catalysts3 Bipyridine N,N′-Dioxides as Lewis Base Catalysts4 Chiral Allylating Reagents5 Synthetic Applications6 Concluding Remarks

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20

Seshadri, Hemalatha, and Carl J. Lovely. "ChemInform Abstract: Application of Olefin Cross-Metathesis to Organometallics. Synthesis of Unsaturated Ferrocenyl Alcohols and Ketones." ChemInform 31, no. 20 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200020154.

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21

Plenio, Herbert, and André Warnecke. "Simple Organometallic Alcohols: Synthesis of (C5H4OH)Mn(CO)3(Hydroxycymantrene) and (C5H4OH)W(CO)3CH3." Organometallics 15, no. 23 (January 1996): 5066–68. http://dx.doi.org/10.1021/om960611t.

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22

Alwarsh, Sefat, Kolawole Ayinuola, Silvana S. Dormi, and Matthias C. McIntosh. "Intercepting the Breslow Intermediate via Claisen Rearrangement: Synthesis of Complex Tertiary Alcohols without Organometallic Reagents." Organic Letters 15, no. 1 (December 5, 2012): 3–5. http://dx.doi.org/10.1021/ol303053c.

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23

Lautens, Mark, Yi Ren, Patrick Delanghe, Pauline Chiu, Shihong Ma, and John Colucci. "1994 Merck Frosst Award Lecture New strategies for the stereoselective synthesis of natural and unnatural products via organometallic reagents and catalysts." Canadian Journal of Chemistry 73, no. 8 (August 1, 1995): 1251–57. http://dx.doi.org/10.1139/v95-153.

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Samarium in the presence of diiodomethane selectively cyclopropanates an allenic alcohol to yield a methylenecyclopropane with modest to excellent diastereoselectivity. The effect of substituents at the carbinol carbon and the allenic carbon on the diastereoselectivity was investigated. A palladium catalyst was shown to promote the intramolecular cycloaddition of the methylenecyclopropane with an electron-deficient alkyne to yield a methylenecyclopentane. The reaction was stereospecific with retention of stereochemistry as proven by X-ray diffraction. Nickel catalysts accelerate the hydroalumination of oxabicyclo[3.2.1]alkenes, leading to bicyclic trialkylalanes. Upon treatment with a Lewis acid (diisobutylaluminum chloride), the trialkylalanes fragment to provide cycloheptenols. This reaction, followed by an enantioselective enzyme-catalyzed esterification, was used as a key step in a synthesis of the mevinic acid lactone. Keywords: methylenecyclopropane, palladium, stereocontrol, oxabicyclic, nickel.

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24

Agami, Claude, Sébastien Comesse, and Catherine Kadouri-Puchot. "Asymmetric Syntheses of New Functionalizedβ-Amino Alcohols via Diastereoselective Addition of Organometallic Reagents onto Oxazolidines." Journal of Organic Chemistry 67, no. 5 (March 2002): 1496–500. http://dx.doi.org/10.1021/jo010779a.

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25

Ukaji, Yutaka, Kouji Yamamoto, Masashi Fukui, and Tamotsu Fujisawa. "Stereodivergent synthesis of optically active tertiary alcohols via addition reaction of chiral 2-acyl oxazolidine with organometallics." Tetrahedron Letters 32, no. 25 (June 1991): 2919–22. http://dx.doi.org/10.1016/0040-4039(91)80649-q.

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26

Alwarsh, Sefat, Kolawole Ayinuola, Silvana S. Dormi, and Matthias C. McIntosh. "ChemInform Abstract: Intercepting the Breslow Intermediate via Claisen Rearrangement: Synthesis of Complex Tertiary Alcohols Without Organometallic Reagents." ChemInform 44, no. 21 (May 2, 2013): no. http://dx.doi.org/10.1002/chin.201321147.

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27

UKAJI, Y., K. YAMAMOTO, M. FUKUI, and T. FUJISAWA. "ChemInform Abstract: Stereodivergent Synthesis of Optically Active Tertiaryl Alcohols via Addition Reaction of Chiral 2-Acyl Oxazolidine With Organometallics." ChemInform 23, no. 13 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199213076.

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28

Agami, Claude, Sebastien Comesse, and Catherine Kadouri-Puchot. "ChemInform Abstract: Asymmetric Syntheses of New Functionalized β-Amino Alcohols via Diastereoselective Addition of Organometallic Reagents onto Oxazolidines." ChemInform 33, no. 31 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200231078.

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29

Wolfe, Saul, Caijun Zhang, Blair D. Johnston, and Chan-Kyung Kim. "Synthesis of the stereoisomers of a novel antibacterial agent and interpretation of their relative activities in terms of a theoretical model of the penicillin receptor." Canadian Journal of Chemistry 72, no. 4 (April 1, 1994): 1066–75. http://dx.doi.org/10.1139/v94-134.

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2,2-Dimethyl-3-(2′-hydroxypropyl)-5-carboxy-Δ3 -1,4-thiazine (1) is a designed antibacterial agent. Based on an analysis of how penicillin complexes to and reacts with a model of a penicillin-binding protein, 1 contains a functional group (C=N) that can react with a serine hydroxyl group of the receptor according to the putative reaction Enz-OH + C = N → Enz-O-C-NH. Compound 1 also contains additional substituents that are designed to position the O-H and C=N groups relative to one another in the enzyme–substrate complex in a geometry that attempts to reproduce the optimum geometry of approach of two such reactants. A most important assumption is that this optimum geometry can be computed ab initio. In a first preparation of 1, (±)-5-methyl-4-hexene-2-ol (2) was converted to the lithium salt of (±)-2-mercapto-2-methyl-5-tert-butyldimethylsiloxy-3- hexanone (7), which was condensed with the N-tert-butoxycarbonyl-D- and L-serine-β-lactones (3). The synthesis was completed by deprotection with formic acid and cyclization in water. The R and S enantiomers of 2 have now been obtained, and the absolute configuration of the alcohol established, by reaction of the R- and S-propylene oxides with an organometallic reagent prepared from β,β-dimethylvinyl bromide. The R alcohol has also been secured by lipase-catalyzed transesterification with trifluoroethyl butyrate, and chemical hydrolysis of the trifluoroethyl ester. The R and S enantiomers of 2 were converted to the R and S enantiomers of 7, and these were condensed with the R and S enantiomers of 3 to yield each of the stereoisomers of the chemically unstable 1 in ca. 95% optically pure form. Antibacterial activity resides in the 5S,8R and 5S,8S isomers. These findings are shown to be consistent with the theoretical model. It is hoped that the stability of the lead structure 1 can be improved, to allow binding experiments with penicillin recognizing enzymes to proceed.

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30

Takeda, Yoshiyuki, Takashi Matsumoto, and Fumie Sato. "Synthesis of optically active .beta.,.gamma.-epoxy alcohols and secondary allylic alcohols via diastereoselective addition of .alpha.-(trimethylsilyl)-.alpha.,.beta.-epoxy aldehydes with organometallic compounds." Journal of Organic Chemistry 51, no. 24 (November 1986): 4728–31. http://dx.doi.org/10.1021/jo00374a047.

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Alberola, Angel, Blanca Calvo, Alfonso Gonz�lez Ortega, and Rafael Pedrosa. "Reaction of 4-chlorocoumarin with organometallic reagents. Synthesis of trialkylbenzopyrans, 4-chlorobenzopyrans, 4-alkylcoumarins and o-hydroxyphenylprop-2-ynyl alcohols." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (1992): 3075. http://dx.doi.org/10.1039/p19920003075.

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32

Armagan, Efe, Shankar Thiyagarajan, Kongchang Wei, Akin Gursoy, Giuseppino Fortunato, Esther Amstad, René Michel Rossi, and Claudio Toncelli. "Reversible Oxygen Sensing Based on Multi-Emission Fluorescence Quenching." Sensors 20, no. 2 (January 15, 2020): 477. http://dx.doi.org/10.3390/s20020477.

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Oxygen is ubiquitous in nature and it plays a key role in several biological processes, such as cellular respiration and food deterioration, to name a few. Currently, reversible and non-destructive oxygen sensing is usually performed with sensors produced by photosensitization of phosphorescent organometallic complexes. In contrast, we propose a novel route of optical oxygen sensing by fluorescence-based quenching of oxygen. We hereby developed for the first time a set of multi-emissive purely organic emitters. These were produced through a one-pot hydrothermal synthesis using p-phenylenediamine (PPD) and urea as starting materials. The origin of the multi-emission has been ascribed to the diversity of chemical structures produced as a result of oxidative oligomerization of PPD. A Bandrowski’s base (BB, i.e., trimer of PPD) is reported as the main component at reaction times higher than 8 h. This indication was confirmed by electrospray-ionization quadrupole time-of-flight (ESI-QTOF) and liquid chromatography-mass spectrometry (LC-MS) analysis. Once the emitters are embedded within a high molecular weight poly (vinyl alcohol) matrix, the intensities of all three emission centers exhibit a non-linear quenching provoked by oxygen within the range of 0–8 kPa. The detection limit of the emission centers are 0.89 kPa, 0.67 kPa and 0.75 kPa, respectively. This oxygen-dependent change in fluorescence emission is reversible (up to three tested 0–21% O2 cycles) and reproducible with negligible cross-interference to humidity. The cost-effectiveness, metal-free formulation, cross-referencing between each single emission center and the relevant oxygen range are all appealing features, making these sensors promising for the detection of oxygen, e.g., in food packaged products.

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Wang, Yi Fong, James J. Lalonde, Milagros Momongan, David E. Bergbreiter, and Chi Huey Wong. "Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars and organometallics." Journal of the American Chemical Society 110, no. 21 (October 1988): 7200–7205. http://dx.doi.org/10.1021/ja00229a041.

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34

ALBEROLA, A., B. CALVO, A. GONZALEZ ORTEGA, and R. PEDROSA. "ChemInform Abstract: Reaction of 4-Chlorocoumarin with Organometallic Reagents. Synthesis of Trialkylbenzopyrans, 4-Chlorobenzopyrans, 4-Alkylcoumarins and o- Hydroxyphenylprop-2-ynyl Alcohols." ChemInform 24, no. 12 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199312166.

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35

Cho, Han Seock, and Wha Young Lee. "Synthesis of inorganic MgCl2–alcohol adduct via recrystallization method and its application in supported organometallic catalysts for the polymerization of ethylene with 1-hexene." Journal of Molecular Catalysis A: Chemical 191, no. 2 (January 2003): 155–65. http://dx.doi.org/10.1016/s1381-1169(02)00215-7.

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36

Hao, Zhiqiang, Ying Li, Chen Li, Ruitao Wu, Zhihong Ma, Suzhen Li, Zhangang Han, Xuezhong Zheng, and Jin Lin. "Synthesis of a series of new ruthenium organometallic complexes derived from pyridine-imine ligands and their catalytic activity in oxidation of secondary alcohols." Applied Organometallic Chemistry 33, no. 3 (December 21, 2018): e4750. http://dx.doi.org/10.1002/aoc.4750.

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37

Esteruelas, Miguel A., Angel V. Gómez, Ana M. López, Montserrat Oliván, Enrique Oñate, and Natividad Ruiz. "Synthesis of Novel Organometallic Compounds Containing η1-Carbon Polycyclic Ligands: Condensation of Propargyl Alcohol with the Allenylidene Ligand of [Ru(η5-C5H5)(CCCPh2)(CO)(PPri3)]BF4." Organometallics 19, no. 1 (January 2000): 4–14. http://dx.doi.org/10.1021/om990456t.

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Bernardi, Luca, Bianca F. Bonini, Elena Capitò, Gabriella Dessole, Cristina Femoni, Mariafrancesca Fochi, Mauro Comes-Franchini, Alessandra Mincio, and Alfredo Ricci. "Diastereoselective additions of organometallic reagents to (SFc)-2-p-tolylsulfanylferrocene carboxyaldehyde and to (SFc)-2-p-tolylsulfanyl ferrocenyl imines. Synthesis of new central and planar chiral ferrocenyl alcohols and amines." Arkivoc 2004, no. 2 (December 14, 2003): 72–90. http://dx.doi.org/10.3998/ark.5550190.0005.206.

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39

Fukuzawa, Shin-ichi, Daisuke Tsuchiya, Kae Sasamoto, Kohki Hirano, and Makoto Ohtaguchi. "ChemInform Abstract: Diastereoselective 1,2-Addition of Organometallic Reagents to Chiral Formylferrocenes Leading to Enantiomerically Pure Ferrocenyl Amino Alcohols: Application to Asymmetric Dialkylzinc Addition to Aldehydes and Synthesis of Optically A." ChemInform 32, no. 4 (January 23, 2001): no. http://dx.doi.org/10.1002/chin.200104038.

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Fukuzawa, Shin-ichi, Daisuke Tsuchiya, Kae Sasamoto, Kohki Hirano, and Makoto Ohtaguchi. "Diastereoselective 1,2-Addition of Organometallic Reagents to Chiral Formylferrocenes Leading to Enantiomerically Pure Ferrocenyl Amino Alcohols: Application to Asymmetric Dialkylzinc Addition to Aldehydes and Synthesis of Optically Active 1,2-Homodisubstituted Ferrocenes." European Journal of Organic Chemistry 2000, no. 16 (August 2000): 2877–83. http://dx.doi.org/10.1002/1099-0690(200008)2000:16<2877::aid-ejoc2877>3.0.co;2-u.

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41

Al-Azmi, Amal, and Sajjad Keshipour. "Cross-linked chitosan aerogel modified with Pd(II)/phthalocyanine: Synthesis, characterization, and catalytic application." Scientific Reports 9, no. 1 (September 25, 2019). http://dx.doi.org/10.1038/s41598-019-50021-6.

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Abstract Palladium(II) phthalocyanine (PdPc) tetrasulfonate was chemically bonded to an amine moiety of chitosan aerogel. The reaction was promoted by the transformation of sulfonic acid groups of PdPc to sulfonyl chloride, which is highly active for amination. The porous composite showed good catalytic activity in the oxidation reaction of some alkylarenes, aliphatic and benzylic alcohols, and cyclohexanol. High conversions and excellent selectivities were obtained for the solvent-free reactions under aerobic conditions at 80 °C during 24 h. While many oxidation reactions have been reported catalysed with palladium phthalocyanine, this is the first reported oxidation of alkylarenes via this catalyst. The organometallic compound is applicable as a heterogeneous catalyst having high chemical stability with recyclability up to six times.

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42

Fu, Qinghong, and Thomas A. P. Seery. "The Synthesis of Liquid Crystalline Polymer on Gold Nanoparticles." MRS Proceedings 661 (2000). http://dx.doi.org/10.1557/proc-661-kk8.7.

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ABSTRACTGold nanoparticles with thiol stabilizing layers were prepared with various fractions of end-functional thiols. Alcohol end-groups were further elaborated to norbornyl moieties so that a ruthenium alkylidene initiator could be tethered to the nanoparticle surfaces. In two different nanoparticle formulations the functional thiols possessed hydrocarbon chains that held the metal centers either near to or far from the surface of the thiol stabilizing layer. The tethered organometallic complexes were used to initiate polymerization from the nanoparticle surfaces. Liquid crystalline polymer was grown from nanoparticles where the metal center was tethered far from the surface but polymerization could not be initiated when the metal centers were held close to the surface. We hypothesize that steric hindrance is controlled by the length of the tethering thiol. Polarized optical microscopy showed that the polymer coated gold nanoparticles could still form a nematic mesophase at elevated temperature although the orientation of mesogens is restricted by crowding at the nanoparticle surface. Samples of unbound polymer were also prepared and exhibited similar transition behavior.

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Alberola, Angel, Celia Andrés, Alfonso González Ortega, Rafael Pedrosa, and Martina Vicente. "Ring opening of 2H-pyrans promoted by organometallic reagents. Synthesis of dienic alcohols." J. Chem. Soc., Perkin Trans. 1, 1987, 2125–28. http://dx.doi.org/10.1039/p19870002125.

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LAROCK, R. C., and S. K. STOLZ-DUNN. "ChemInform Abstract: Synthesis of Homoallylic Alcohols via Organometallic Ring Opening of Vinylic Oxetanes." ChemInform 21, no. 51 (December 18, 1990). http://dx.doi.org/10.1002/chin.199051124.

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45

Sychevsky, М., К. Danilova, and S. Oliynichuk. "THE INFLUENCE OF NANOPARTICLES OF BIOGENIC METALS ON CULTURING THE YEAST SACCHAROMYCES СEREVISIAE." Food Science and Technology 14, no. 3 (May 29, 2020). http://dx.doi.org/10.15673/fst.v14i3.1610.

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The effect of nanoparticles of biogenic metals (Fe, Mg, Zn, Mn) and their combinations on culturing the yeast Saccharomyces cerevisiae and on fermentation of sugar-containing raw materials into ethanol have been investigated . The research involved the use of nanometal preparations obtained by volumetric electric-spark dispersion. It has proved effective to add nanozinc and a preparation containing nanomanganese and nanomagnesium, prior to yeast cultivation, to the growth media agar and wort agar in the concentrations 0.5 μg/cm3 and 11 μg/cm3 respectively. The experimental yeast grown on the medium containing these preparations increased the alcohol concentration in the distiller’s wort by 0.2%, whereas the content of unfermented carbohydrates remained within the prescribed limits 0.32–0.39 g/100 сm3. The yeast biomass increased by 1.2–1.4 times. Zinc and manganese/magnesium nanopreparations increased the maltase and invertase activities of the yeast under study by 40–25%. The nanoiron preparation contributed to inhibiting the fermentation activity of the yeast biomass. Biogenic metal nanocomplexes are used by yeast as an additional nutrient source. They form organometallic and intracomplex active compounds with yeast cell enzymes, primarily with hexokinase, aldolase, enolase. This intensifies synthesis of enzymes and increases their catalytic effect. The results obtained prove the effectiveness of biogenic metal nanopreparations as catalysts for biochemical transformations in a yeast cell. Using nanometals increases the productivity of bakery yeast, improves the technological process of alcoholic fermentation, and offers ample opportunity to increase the activity of enzyme preparations in the course of their production.

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46

Yus, M., C. Najera, and R. Chinchilla. "ChemInform Abstract: Carboxylic Acid Esters: Synthesis from Organometallic Compounds, Alkyl Halides, Primary Alcohols, or Ethers." ChemInform 39, no. 49 (December 2, 2008). http://dx.doi.org/10.1002/chin.200849263.

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47

ALBEROLA, A., C. ANDRES, A. GONZALEZ ORTEGA, R. PEDROSA, and M. VICENTE. "ChemInform Abstract: Ring-Opening of 2H-Pyrans Promoted by Organometallic Reagents. Synthesis of Dienic Alcohols." ChemInform 19, no. 4 (January 26, 1988). http://dx.doi.org/10.1002/chin.198804080.

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48

Hatano, Manabu, and Kazuaki Ishihara. "ChemInform Abstract: Recent Progress in the Catalytic Synthesis of Tertiary Alcohols from Ketones with Organometallic Reagents." ChemInform 39, no. 37 (September 9, 2008). http://dx.doi.org/10.1002/chin.200837250.

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49

Roquero, Pedro, Luis Carlos Ordóñez, Omar Herrera, Orlando Ugalde, and Jorge Ramírez. "Synthesis and Characterization of Carbon-Supported Platinum-Molybdenum and Platinum-Tungsten Catalysts for Methanol Oxidation in Direct Alcohol Fuel Cells." International Journal of Chemical Reactor Engineering 5, no. 1 (November 15, 2007). http://dx.doi.org/10.2202/1542-6580.1491.

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A series of carbon-supported bimetallic catalysts with different metallic loadings was synthesized, using platinum as the principal active phase and molybdenum or tungsten as promoting phases. The materials were prepared by organometallic precursor thermolysis and characterized by direct current electrochemical methods, transmission electron microscopy, scanning electron microscopy and x-ray diffraction. Electrodes were elaborated with each catalyst and their electrochemical performances were studied by cyclic voltammetry. These results show an increased activity of the catalysts with small amounts of Mo or W, towards oxidation of methanol with respect to the catalyst containing only platinum. XRD results reveal the presence of molybdenum or tungsten bronzes (HxMoO3, HxWO3) that are responsible for the increase in activity. It is believed that the bronzes participate in a spillover effect by promoting the removal of protons from the platinum surface. It was found that the presence of molybdenum in this type of catalyst prevents the platinum phase from sintering during the thermal treatment and allows them to keep platinum particles with mean sizes between 2 and 8 nm. The proposed catalysts are adequate for methanol oxidation in liquid-fuel alcohol fuel cell systems, since it was found that oxidation potentials are lower than those observed with platinum catalysts.

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50

TAKEDA, Y., T. MATSUMOTO, and F. SATO. "ChemInform Abstract: Synthesis of Optically Active β,γ-Epoxy Alcohols and Secondary Allylic Alcohols via Diastereoselective Addition of α-Trimethylsilyl-α,β-epoxy Aldehydes with Organometallic Compounds." ChemInform 18, no. 24 (June 16, 1987). http://dx.doi.org/10.1002/chin.198724145.

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