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Littérature scientifique sur le sujet « Tandem photochemical reaction »

Auteur : Grafiati

Publié le 2 novembre 2024

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Articles de revues sur le sujet "Tandem photochemical reaction"

Saunthwal, Rakesh K., James Mortimer, Andrew J. Orr-Ewing et Jonathan Clayden. « Enantioselective one-carbon expansion of aromatic rings by simultaneous formation and chromoselective irradiation of a transient coloured enolate ». Chemical Science 13, n^o 7 (2022) : 2079–85. http://dx.doi.org/10.1039/d1sc06684f.

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Irradiation of a mixture of aromatic amide and chiral base leads to a tandem reaction sequence in which dearomatization forms a chromophore capable of photochemical rearrangement leading to overall asymmetric expansion of the aromatic ring.

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Hoffmann, Norbert, Samuel Bertrand, Siniša Marinković et Jens Pesch. « Efficient radical addition of tertiary amines to alkenes using photochemical electron transfer ». Pure and Applied Chemistry 78, n^o 12 (1 janvier 2006) : 2227–46. http://dx.doi.org/10.1351/pac200678122227.

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An efficient photoinduced radical addition of tertiary amine, mainly cyclic derivatives, to electron-deficient alkenes was developed. The reaction was applied to the asymmetric synthesis of the pyrrolizidine alkaloids laburnine and isoretronecanol. The method was then optimized for the addition of a larger variety of tertiary amines, in particular acyclic ones. Radical tandem addition cyclization reactions with unsaturated tertiary amines have also been investigated. A detailed mechanistic study using isotopic labeling enabled the optimization of a corresponding reaction with N,N-dialkylaniline derivatives. The origin of the high reaction stereoselectivity achieved with menthyloxyfuranone was elucidated. The radical addition of tertiary amines was also performed with heterogeneous photocatalysis using inorganic semiconductors as sensitizers.

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Chiminelli, Maurizio, Gabriele Scarica, Andrea Serafino, Luciano Marchiò, Rosanna Viscardi et Giovanni Maestri. « Visible-Light-Promoted Tandem Skeletal Rearrangement/Dearomatization of Heteroaryl Enallenes ». Molecules 29, n^o 3 (25 janvier 2024) : 595. http://dx.doi.org/10.3390/molecules29030595.

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Access to complex three-dimensional molecular architectures via dearomatization of ubiquitous aryl rings is a powerful synthetic tool, which faces, however, an inherent challenge to overcome energetic costs due to the loss of aromatic stabilization energy. Photochemical methods that allow one to populate high-energy states can thus be an ideal strategy to accomplish otherwise prohibitive reaction pathways. We present an original dearomative rearrangement of heteroaryl acryloylallenamides that leads to complex fused tricycles. The visible-light-promoted method occurs under mild conditions and tolerates a variety of functional groups. According to DFT modeling used to rationalize the outcome of the cascade, the reaction involves a sequential [2+2] allene–alkene photocycloaddition, which is followed by a selective retro- [2+2] step that paves the way for the dearomatization of the heteroaryl partner. This scenario is original with respect to the reported photochemical reactivity of similar substrates and thus holds promise for ample future developments.

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Hou, Yunyan, et Peter Wan. « A pentacene intermediate via formal intramolecular photoredox of a 6,13-pentacenequinone in aqueous solution ». Canadian Journal of Chemistry 85, n^o 12 (1 décembre 2007) : 1023–32. http://dx.doi.org/10.1139/v07-117.

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The formal intramolecular photoredox reaction (or tandem phototautomerizations) of aromatic ketones in aqueous solution discovered in our laboratory has been extended to a number of acenequinones. In particular, we were interested in whether the photoredox reaction could be applied to 2-(hydroxymethyl)-6,13-pentacenequinone (4), which would result in 2-formyl-6,13-dihydroxypentacene (10) and hence offer a photochemical method for synthesizing a pentacene derivative. Whereas a number of acenequinones displayed a range of photoredox reactivity, photolysis of 4 in acidic aqueous solution (pH < 3) resulted in a clean intramolecular photoredox reaction, via an enol intermediate, to give 10 (green compound; Φ ~ 0.2 at pH 1), which was too reactive for isolation or trapping by standard ArOH trapping agents such as acetic anhydride. These reactions may be viewed as a one-way photochemical intramolecular “redox switch” from quinone to hydroquinone with concurrent oxidation of an attached hydroxymethyl (alcohol) moiety. Without the attached alcohol moiety, these acenequinones are photostable in aqueous solution. The trend in observed relative reactivity may be partially rationalized by examining changes in molecular orbital coefficients observed in the calculated HOMOs and LUMOs (at the AM1 level).Key words: pentacene, acenequinones, photoredox, enol, acid catalysis.

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Liang, Yan Ru, Yu Yun Wen, Xiao Yan Hong, Zhen Bin Gong et Wen Quan Li. « Laboratory Simulation Study of Photo-Degradation Process of Fenvalerate in Aqueous Solution ». Applied Mechanics and Materials 312 (février 2013) : 886–92. http://dx.doi.org/10.4028/www.scientific.net/amm.312.886.

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A laboratory-made the efficient photochemical degradation experimental device, combined with high performance liquid chromatography-tandem diode array detector device (DAD), fluorescence detector (FLD), mass spectrometer detector (MS), research fenvalerate its photo degradation. The structure of the spectral characteristics is the product, photo degradation reaction kinetics of degradation products, suggesting fenvalerate light chemical degradation process in an aqueous solution. The spectral characteristics of fenvalerate under ultraviolet light can be degraded into smaller organic molecules; maternal and main product have strong UV - visible absorption, fenvalerate are weakly fluorescent substance in the aqueous solution. The major products are strong fluorescent substance. Almost no effect The photo degradation kinetic data show fenvalerate photo degradation in an aqueous solution to approximate a reaction of the reaction; pesticide initial concentration, the pH value of the aqueous solution of pesticides photo degradation reaction rate; To accelerate the increase of salinity, light intensity fenvalerate in aqueous photo degradation reaction rate; significant influence of small organic molecules, with the type of small organic molecules.

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Ren, Jia, Elissia T. Franklin et Yu Xia. « Uncovering Structural Diversity of Unsaturated Fatty Acyls in Cholesteryl Esters via Photochemical Reaction and Tandem Mass Spectrometry ». Journal of The American Society for Mass Spectrometry 28, n^o 7 (17 avril 2017) : 1432–41. http://dx.doi.org/10.1007/s13361-017-1639-6.

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Li, Hai-Fang, Jing Zhao, Wenbo Cao, Wenpeng Zhang, Yu Xia et Zheng Ouyang. « Site-Specific Photochemical Reaction for Improved C=C Location Analysis of Unsaturated Lipids by Ultraviolet Photodissociation ». Research 2022 (12 février 2022) : 1–12. http://dx.doi.org/10.34133/2022/9783602.

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Unraveling the complexity of the lipidome requires the development of novel approaches to facilitate structural identification and characterization of lipid species with isomer-level discrimination. Ultraviolet photodissociation tandem mass spectrometry (UVPD MS/MS) is a promising tool for structure determination of lipids. The sensitivity of UVPD for lipid analysis however is limited mainly due to weak absorption of UV photons by a C=C. Herein, a C=C site-specific derivatization, the Paternò-Büchi (PB) reaction, was used to incorporate a chromophore to the C=C moiety in fatty acyls, leading to significantly improved UVPD efficiency and sensitivity for pinpointing C=C locations. The wavelength-dependent photodissociation of the PB products demonstrated 4-CF3-benzophenone as the best reagent for UVPD in terms of the efficiency of generating C=C diagnostic fragments and simplicity for C=C location assignments. We demonstrated the effectiveness of this approach for the shotgun profiling of C=C location isomers in different lipid classes from complex lipid extracts, highlighting its potential to advancing the identification of the C=C bond locations in unsaturated lipids.

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Ma, Xiaoxiao, Leelyn Chong, Ran Tian, Riyi Shi, Tony Y. Hu, Zheng Ouyang et Yu Xia. « Identification and quantitation of lipid C=C location isomers : A shotgun lipidomics approach enabled by photochemical reaction ». Proceedings of the National Academy of Sciences 113, n^o 10 (22 février 2016) : 2573–78. http://dx.doi.org/10.1073/pnas.1523356113.

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The field of lipidomics has been significantly advanced by mass spectrometric analysis. The distinction and quantitation of the unsaturated lipid isomers, however, remain a long-standing challenge. In this study, we have developed an analytical tool for both identification and quantitation of lipid C=C location isomers from complex mixtures using online Paternò–Büchi reaction coupled with tandem mass spectrometry (MS/MS). The potential of this method has been demonstrated with an implementation into shotgun lipid analysis of animal tissues. Among 96 of the unsaturated fatty acids and glycerophospholipids identified from rat brain tissue, 50% of them were found as mixtures of C=C location isomers; for the first time, to our knowledge, the quantitative information of lipid C=C isomers from a broad range of classes was obtained. This method also enabled facile cross-tissue examinations, which revealed significant changes in C=C location isomer compositions of a series of fatty acids and glycerophospholipid (GP) species between the normal and cancerous tissues.

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Janechek, Nathan J., Rachel F. Marek, Nathan Bryngelson, Ashish Singh, Robert L. Bullard, William H. Brune et Charles O. Stanier. « Physical properties of secondary photochemical aerosol from OH oxidation of a cyclic siloxane ». Atmospheric Chemistry and Physics 19, n^o 3 (8 février 2019) : 1649–64. http://dx.doi.org/10.5194/acp-19-1649-2019.

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Abstract. Cyclic volatile methyl siloxanes (cVMS) are high-production chemicals present in many personal care products. They are volatile, hydrophobic, and relatively long-lived due to slow oxidation kinetics. Evidence from chamber and ambient studies indicates that oxidation products may be found in the condensed aerosol phase. In this work, we use an oxidation flow reactor to produce ∼100 µg m−3 of organosilicon aerosol from OH oxidation of decamethylcyclopentasiloxane (D5) with aerosol mass fractions (i.e., yields) of 0.2–0.5. The aerosols were assessed for concentration, size distribution, morphology, sensitivity to seed aerosol, hygroscopicity, volatility and chemical composition through a combination of aerosol size distribution measurement, tandem differential mobility analysis, and electron microscopy. Similar aerosols were produced when vapor from solid antiperspirant was used as the reaction precursor. Aerosol yield was sensitive to chamber OH and to seed aerosol, suggesting sensitivity of lower-volatility species and recovered yields to oxidation conditions and chamber operation. The D5 oxidation aerosol products were relatively non-hygroscopic, with an average hygroscopicity kappa of ∼0.01, and nearly non-volatile up to 190 ∘C temperature. Parameters for exploratory treatment as a semi-volatile organic aerosol in atmospheric models are provided.

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Bertrand, Samuel, Norbert Hoffmann, Jean-Pierre Pete et Véronique Bulach. « Stereoselective radical-tandem reaction of aniline derivatives with (5R)-5-menthyloxy-2,5-dihydrofuran-2-one initiated by photochemical induced electron transfer ». Chemical Communications, n^o 22 (1999) : 2291–92. http://dx.doi.org/10.1039/a906051k.

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Thèses sur le sujet "Tandem photochemical reaction"

Yu, Xiaodan. « New functionalized alkylidenecyclobutanes : multicomponent synthesis and applications ». Electronic Thesis or Diss., université Paris-Saclay, 2024. http://www.theses.fr/2024UPASF034.

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Les dérivés du cyclobutane sont devenus de plus en plus importants en tant que blocs de construction moléculaires en raison de leur contrainte cyclique inhérente et de la modification sélective de leurs structures qui peuvent être utilisées de manière stratégique dans la synthèse organique. Les cycles cyclobutane apparaissent également dans les structures moléculaires d'un large panel de molécules naturelles et synthétiques qui présentent des activités biologiques intéressantes. Au sein de cette grande famille, les sous-unités alkylidènecyclobutane sont rencontrées dans des produits naturels, tels que la providencine, et elles présentent une réactivité accrue permettant d'accéder à des structures moléculaires complexes, notamment des dérivés cyclobutane à cycle élargi et hautement fonctionnalisés. Dans notre laboratoire, nous avons récemment développé une synthèse efficace de cyclobutènes fonctionnalisés par une réaction domino photochimique à partir de cyclopent-2-énones et d'éthylène. Sur la base de cette étude, nous avons d'abord exploré une transformation simple de cyclobutènes fonctionnalisés en alkylidènecyclobutanes. Ensuite, nous avons combiné les deux séquences dans un processus domino à plusieurs composants. La réaction domino-MCR est réalisée selon un protocole unique, comprenant une réaction photochimique en tandem de cycloaddition [2+2] / Norrish-I / γ-H suivie d'une réaction de protection acétal et d'une réaction de substitution allylique. De plus, la version intramoléculaire de ces réactions a permis la synthèse d'alkylidènecyclobutanes bicycliques fusionnés complexes. Enfin, la post-fonctionnalisation des alkylidènecyclobutanes a été étudiée, dans le but de découvrir le nouveau composé tricyclique fusionné par un processus photochimique intramoléculaire [2+2]
Cyclobutane derivatives have become increasingly important as molecular building blocks because of their inherent ring strain that facilitates the selective modification of their structures for strategic used in organic synthesis. Cyclobutane rings also appear in the molecular structures of a wide panel of natural and synthetic molecules that display interesting biological activities. Within this large family, alkylidenecyclobutane subunits are encountered in natural products, such as providencin, and they exhibit enhanced reactivity providing access to complex molecular structures, including enlarged ring and highly functionalized cyclobutane derivatives. In our laboratory, we recently developed an efficient synthesis of functionalized cyclobutenes through a domino photochemical reaction starting from cyclopent-2-enones and ethylene. Based on this study, we first explored a straight-forward transformation of functionalized cyclobutenes into alkylidenecyclobutanes. We then combined both sequences in a domino-multicomponent process. This was accomplished in a single protocol, comprising a tandem photochemical [2+2]-cycloaddition / Norrish-I / γ-H transfer reaction followed by an acetal-protection and an allylic substitution reaction. Additionally, the intramolecular version of these reactions allowed the synthesis of complex fused-bicyclic alkylidenecyclobutanes. Finally, the post-funtionalization of selected alkylidenecyclobutanes was studied, aiming to prepare novel fused tricyclic compounds through a intramolecular [2+2] photochemical process

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(5929454), Sarju Adhikari. « RADICAL CHEMISTRY AND MASS SPECTROMETRY FOR ENHANCED BIOMOLECULE ANALYSIS ». Thesis, 2019.

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Electrospray ionization-tandem mass spectrometry (ESI-MS/MS) has been established as a powerful tool for qualitative and quantitative analysis of biomolecules. However, mass spectrometric analysis of biomolecules is often limited by poor ionization efficiency of analyte for sensitive detection and limited fragmentation for structural characterization. Over the years, various solution phase as well as gas-phase derivatization techniques, have been coupled with MS to increase the ionization efficiency and facilitate the formation of structural informative fragment ions. The research presented in this dissertation falls into two major parts; focusing on method development and application of radical chemistry for enhanced biomolecule analysis on an ESI-MS/MS platform. In the first part, a method of rapid charge tagging of neutral lipids (e.g. sterols, glycerides) with a thiol radical-based charge tag is developed, followed by comprehensive analysis via ESI-MS/MS without the use of a chromatographic separation (shotgun lipidomics). This charge tagging is performed in an easily constructible fused silica capillary-based microflow photo-reactor which is relatively low in cost and requires no instrument modifications. This method significantly enhances the ionization efficiency of the neutral lipids for sensitive MS detection (pM range). This method can be applied to the small volume of biological complex samples (e.g. 1 µL plasma) and doesn’t require extensive sample pretreatment procedure (analysis time of 2 min vs. traditional >60 min on GC-MS and HPLC-MS systems). Furthermore, the derivatized neutral lipids can also be fragmented via soft collision-induced dissociation to obtain fatty acyl chain composition of the neutral lipids (sterol esters, diacylglycerols, triacylglycerols, etc.) for structural characterization. This can especially be useful for determination for fatty acyl compositional isomers in neutral lipids for analysis related to biomarker detection. The characteristic fragmentation pattern of tagged neutral lipids has also been utilized for quantitation of lipids from biological mixture samples. Initial application of this method has shown alteration in the concentration of diacylglycerol lipid species in clinical samples of Type 2 Diabetes Mellitus patients, suggesting the potential of understanding the biological roles of such lipids in insulin resistance.

In the second part, a unique approach of radical-induced disulfide bond cleavage in peptides and proteins is demonstrated. Using 254 nm UV emission, acetone was used as a photoinitiator to initiate secondary radical formation i.e. hydroxyalkyl radical, from alcohol co-solvents used for electrospray. These radicals can then be used to efficiently cleave the disulfide bonds (R-S-S-R) in peptide/proteins to give reduced reaction products (RSH) at the cleavage site. Upon soft collision-induced dissociation, the reduced product gave abundant b- and y- type fragment ions for complete or enhanced sequence coverage as compared to intact disulfide-linked peptides and proteins. With the use of a simple microflow photo-reactor, this radical based approach can also be coupled with infusion ESI-MS/MS for a rapid online-based peptide and protein analysis. The yield for disulfide bond reduction was almost 100% within less than 5 s of UV irradiation. Furthermore, by adjusting the UV irradiance time, different degrees of partial reduction could be achieved, which greatly facilitated the disulfide linkage mapping in peptides and proteins with multiple disulfide bonds. This method has been incorporated with both bottom-up and top-down approach for protein analysis for unraveling the molecular complexity, quantifying and deep sequencing of disulfide-linked proteins.

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Chapitres de livres sur le sujet "Tandem photochemical reaction"

Winkler, J. D., R. D. Scott et P. G. Williard,. « Synthesis of a Vindorosine Precursor ». Dans Exercises in Synthetic Organic Chemistry, 93. Oxford University PressOxford, 1997. http://dx.doi.org/10.1093/oso/9780198559443.003.0067.

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Abstract Discussion Points What is the mechanism of the protection sequence a, b? Explain the steroselectivities observed in the photochemical reaction of step f and in the Mannich reaction step g. What is the purpose of tetrabutylammonium fluoride in step h? What is the byproduct of step k? Further Reading For reviews on tandem reaction in the synthesis of natural products, see P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev.,1996, 96,195; J. D. Winkler, C. M. Bowen and F. Liotta, Chem. Rev.,1995, 95,2003.

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Lambert, Tristan H. « Flow Chemistry ». Dans Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0017.

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Timothy F. Jamison at MIT developed (Org. Lett. 2013, 15, 710) a metal-free continuous-flow hydrogenation of alkene 1 using the protected hydroxylamine reagent 2 in the presence of free hydroxylamine. The reduction of nitroindole 4 to the corresponding aniline 5 using in situ-generated iron oxide nanocrystals in continuous flow was reported (Angew. Chem. Int. Ed. 2012, 51, 10190) by C. Oliver Kappe at the University of Graz. A flow method for the MPV reduction of ketone 6 to alcohol 7 was disclosed (Org. Lett. 2013, 15, 2278) by Steven V. Ley at the University of Cambridge. Corey R.J. Stephenson, now at the University of Michigan, developed (Chem. Commun. 2013, 49, 4352) a flow deoxygenation of alcohol 8 to yield 9 using visible light photoredox catalysis. Stephen L. Buchwald at MIT demonstrated (J. Am. Chem. Soc. 2012, 134, 12466) that arylated acetaldehyde 11 could be generated from aminopyridine 10 by diazonium formation and subsequent Meerwein arylation of ethyl vinyl ether in flow. The team of Takahide Fukuyama and Ilhyong Ryu at Osaka Prefecture University showed (Org. Lett. 2013, 15, 2794) that p-iodoanisole (12) could be converted to amide 13 via low-pressure carbonylation using carbon monoxide generated from mixing formic and sulfuric acids. The continuous-flow Sonogashira coupling of alkyne 14 to produce 15 using a Pd-Cu dual reactor was developed (Org. Lett. 2013, 15, 65) by Chi-Lik Ken Lee at Singapore Polytechnic. A tandem Sonogashira/cycloisomerization procedure to convert bromopyridine 16 to aminoindolizine 18 in flow was realized (Adv. Synth. Cat. 2012, 354, 2373) by Keith James at Scripps, La Jolla. A procedure for the Pauson-Khand reaction of alkene 19 to produce the bicycle 20 in a photochemical microreactor was reported (Org. Lett. 2013, 15, 2398) by Jun-ichi Yoshida at Kyoto University. Kevin I. Booker-Milburn at the University of Bristol discovered (Angew. Chem. Int. Ed. 2013, 52, 1499) that irradiation of N-butenylpyrrole 21 in flow produced the rearranged tricycle 22. Professor Jamison described (Angew. Chem. Int. Ed. 2013, 52, 4251) a unique peptide coupling involving the photochemical rearrangement of nitrone 23 to the hindered dipeptide 24 in continuous flow.

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Taber, Douglass F. « Reactions of Alkenes ». Dans Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0028.

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Ana C. Fernandes of the Instituto Superior Técnico, Lisboa, devised (Tetrahedron Lett. 2010, 51, 1048) an effective Re catalyst for the solvent-free hydrogenation of an alkene 1. Yasushi Imada and Takeshi Naota of Osaka University showed (Organic Lett. 2010, 12, 32) that a flavin could catalyze the hydrogenation of an alkene 3. Note that the thioether was stable under these conditions. Huanfeng Jian of the South China University of Technology developed (J. Org. Chem. 2010, 75, 2321) a Pd-based protocol for the oxidative cleavage of an alkene 5. The cleavage could be halted at the cis diol. K. C. Nicolaou of Scripps/La Jolla optimized (Organic Lett. 2010, 12, 1552) a complemetary cleavage of an alkene 7, again proceeding via the diol. J. R. Falck of UT Southwestern established (J. Org. Chem. 2010, 75, 1701) the Heck-type oxidative silylation of an alkene 9 to the Z -silane 10. Timothy F. Jamison of MIT effected (Chem. Commun. 2010, 46, 907) the borylation of an alkene 11. Kálmán Szabó of Stockholm University reported (Angew. Chem. Int. Ed. 2010, 49, 4051) a complementary approach for effecting the same transformation. Cathleen M. Crudden of Queen’s University, Kingston, observed (J. Am. Chem. Soc. 2010, 132, 131) that Rh-catalyzed hydroboration of 13 delivered the borane 14. Tehshik P. Yoon of the University of Wisconsin used (J. Am. Chem. Soc. 2010, 132, 4570) Fe to catalyze the addition of an oxaziridine 16 to an alkene 15. Yasuhiro Shiraishi of Osaka University improved (J. Org. Chem. 2010, 75, 1450) the photochemical addition of acetone to an alkene 18. Chul-Ho Jun of Yonsei University described (Tetrahedron Lett. 2010, 51, 160) a related procedure. Professor Jamison effected (J. Am. Chem. Soc. 2010, 132, 6880) the branching homologation of an alkene to give 21 . F. Dean Toste of the University of California, Berkeley, accomplished (J. Am. Chem. Soc. 2010, 132, 8885) the oxidative homologation of an alkene to the ester 22. Markus R. Heinrich of the Universität Erlangen-Nürnberg developed (Tetrahedron Lett. 2010, 51, 1758) the tandem addition of the hydroperoxide 23 and a diazonium salt 24, leading to 25.

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