Relevant bibliographies by topics / Indoline, aldehyde and C-H activation

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Academic literature on the topic 'Indoline, aldehyde and C-H activation'

Author: Grafiati
Published: 6 September 2023

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Journal articles on the topic "Indoline, aldehyde and C-H activation"

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Jafarpour, Farnaz, Azizollah Habibi, and Mehran Ghasemi. "Palladium/Norbornene Chemistry in the Synthesis of Polycyclic Indolines with Simple Nitrogen Sources." Synthesis 52, no. 14 (March 27, 2020): 2092–98. http://dx.doi.org/10.1055/s-0039-1707988.

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An efficient procedure has been developed to synthesize ­indoline derivatives through a palladium-catalyzed Heck reaction/C–H activation/dual amination cascade in one pot. This constitutes the first intermolecular catalytic approach to directly access N-alkylindolines with a broad substrate scope in the absence of any ligands. This method highlights the use of readily available amines and ureas as the required nitrogen sources in building up the indoline core.
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Swamy, V. S. V. S. N., K. Vipin Raj, Kumar Vanka, Sakya S. Sen, and Herbert W. Roesky. "Silylene induced cooperative B–H bond activation and unprecedented aldehyde C–H bond splitting with amidinate ring expansion." Chemical Communications 55, no. 24 (2019): 3536–39. http://dx.doi.org/10.1039/c9cc00296k.

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Xu, Pan, Guoqiang Wang, Zhongkai Wu, Shuhua li, and Chengjian Zhu. "Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis." Chemical Science 8, no. 2 (2017): 1303–8. http://dx.doi.org/10.1039/c6sc03888c.

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Yuan, Yumeng, Xiemin Guo, Xiaofeng Zhang, Buhong Li, and Qiufeng Huang. "Access to 5H-benzo[a]carbazol-6-ols and benzo[6,7]cyclohepta[1,2-b]indol-6-ols via rhodium-catalyzed C–H activation/carbenoid insertion/aldol-type cyclization." Organic Chemistry Frontiers 7, no. 20 (2020): 3146–59. http://dx.doi.org/10.1039/d0qo00820f.

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Maia da Silva Santos, Bruno, Mariana dos Santos Dupim, Cauê Paula de Souza, Thiago Messias Cardozo, and Fernanda Gadini Finelli. "DABCO-promoted photocatalytic C–H functionalization of aldehydes." Beilstein Journal of Organic Chemistry 17 (December 21, 2021): 2959–67. http://dx.doi.org/10.3762/bjoc.17.205.

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Herein we present a direct application of DABCO, an inexpensive and broadly accessible organic base, as a hydrogen atom transfer (HAT) abstractor in a photocatalytic strategy for aldehyde C–H activation. The acyl radicals generated in this step were arylated with aryl bromides through a well stablished nickel cross-coupling methodology, leading to a variety of interesting aryl ketones in good yields. We also performed computational calculations to shine light in the HAT step energetics and determined an optimized geometry for the transition state, showing that the hydrogen atom transfer between aldehydes and DABCO is a mildly endergonic, yet sufficiently fast step. The same calculations were performed with quinuclidine, for comparison of both catalysts and the differences are discussed.
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Zhang, Qiao, Angela Bell-Taylor, Fraser M. Bronston, John D. Gorden, and Christian R. Goldsmith. "Aldehyde Deformylation and Catalytic C–H Activation Resulting from a Shared Cobalt(II) Precursor." Inorganic Chemistry 56, no. 2 (December 22, 2016): 773–82. http://dx.doi.org/10.1021/acs.inorgchem.6b02127.

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Török, Patrik, Dóra Lakk-Bogáth, and József Kaizer. "Stoichiometric Alkane and Aldehyde Hydroxylation Reactions Mediated by In Situ Generated Iron(III)-Iodosylbenzene Adduct." Molecules 28, no. 4 (February 15, 2023): 1855. http://dx.doi.org/10.3390/molecules28041855.

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Previously synthesized and spectroscopically characterized mononuclear nonheme, low-spin iron(III)-iodosylbenzene complex bearing a bidentate pyridyl-benzimidazole ligands has been investigated in alkane and aldehyde oxidation reactions. The in situ generated Fe(III) iodosylbenzene intermediate is a reactive oxidant capable of activating the benzylic C-H bond of alkane. Its electrophilic character was confirmed by using substituted benzaldehydes and a modified ligand framework containing electron-donating (Me) substituents. Furthermore, the results of kinetic isotope experiments (KIE) using deuterated substrate indicate that the C-H activation can be interpreted through a tunneling-like HAT mechanism. Based on the results of the kinetic measurements and the relatively high KIE values, we can conclude that the activation of the C-H bond mediated by iron(III)–iodosylbenzene adducts is the rate-determining step.
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Seo, Jia, Che-Wei Chen, Shih-Ching Chuang, Jung Min Joo, Woohyeong Lee, Ju Eun Jeon, and Pei-Ling Chen. "Palladium-Catalyzed C–H Benzannulation of Functionalized Furans and Pyrroles with Alkynes." Synthesis 53, no. 17 (May 6, 2021): 3001–10. http://dx.doi.org/10.1055/a-1502-3641.

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AbstractA benzannulation strategy involving activation of two C–H bonds of five-membered heteroarenes was developed. Readily available furans and pyrroles stabilized by synthetically useful electron-withdrawing groups underwent Pd-catalyzed 1:2 annulation reactions with diaryl alkynes. A variety of functional groups, including ester, amide, ketone, aldehyde, and nitrile, on the heterocyclic cores were tolerated in the Pd-catalyzed oxidative reactions. In these reactions, the combination of 2,2-dimethylbutyric acid and its conjugate base facilitated metalation at the heteroaromatic rings and reoxidation of the Pd(0) species using oxygen as the terminal oxidant. This strategy provides fluorescent ­benzofuran and indole derivatives and is expected to allow for further development of functionalized polycyclic heteroaromatic compounds.
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Massouh, Joe, Antoine Petrelli, Virginie Bellière‐Baca, Damien Hérault, and Hervé Clavier. "Rhodium(III)‐Catalyzed Aldehyde C−H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis." Advanced Synthesis & Catalysis 364, no. 4 (December 29, 2021): 831–37. http://dx.doi.org/10.1002/adsc.202101099.

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Bertini, Simone, and Martin Albrecht. "O-Functionalised NHC Ligands for Efficient Nickel-catalysed C–O Hydrosilylation." CHIMIA International Journal for Chemistry 74, no. 6 (June 24, 2020): 483–88. http://dx.doi.org/10.2533/chimia.2020.483.

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A series of C,O-bidentate chelating mesoionic carbene nickel(ii) complexes [Ni(NHC^PhO)2] (NHC = imidazolylidene or triazolylidene) were applied for hydrosilylation of carbonyl groups. The catalytic system is selective towards aldehyde reduction and tolerant to electron-donating and -withdrawing group substituents. Stoichiometric experiments in the presence of different silanes lends support to a metal–ligand cooperative activation of the Si–H bond. Catalytic performance of the nickel complexes is dependent on the triazolylidene substituents. Butyl-substituted triazolylidene ligands impart turnover numbers up to 7,400 and turnover frequencies of almost 30,000 h-1, identifying this complex as one of the best-performing nickel catalysts for hydrosilylation and demonstrating the outstanding potential of O-functionalised NHC ligands in combination with first-row transition metals.
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Dissertations / Theses on the topic "Indoline, aldehyde and C-H activation"

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Chudasama, V. "The use of aerobic aldehyde C-H activation for the construction of C-C and C-N bonds." Thesis, University College London (University of London), 2011. http://discovery.ucl.ac.uk/1324525/.

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This thesis describes a series of studies directed towards the use of aerobic aldehyde C-H activation for the construction of C-C and C-N bonds by the process of hydroacylation. Chapter 1 provides an introduction to the research project and an overview of strategies for hydroacylation. Chapter 2 describes the application of aerobic aldehyde C-H activation for the hydroacylation of vinyl sulfonates and sulfones. A discussion on the mechanism of the transformation, the effect of using aldehydes with different oxidation profiles and the application of chiral aldehydes is also included. Chapter 3 describes the functionalisation of γ-keto sulfonates with particular emphasis on an elimination/conjugate addition strategy, which provides an indirect approach to the hydroacylation of electron rich alkenes. Chapters 4 and 5 describe the application of aerobic aldehyde C-H activation towards the hydroacylation of α,β-unsaturated esters and vinyl phosphonates, respectively. An in-depth discussion on the mechanism and aldehyde tolerance of each transformation is also included. Chapter 6 describes acyl radical approaches towards C-N bond formation with particular emphasis on the synthesis of amides and acyl hydrazides.
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Hande, Akshay. "Regioselective C-H Amidation Reactions using Directing Group Strategy and its Application in Organic Synthesis." Thesis, 2019. https://etd.iisc.ac.in/handle/2005/4532.

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The thesis represents an approach for the C-H bond activation using directing group strategy. The C-H activation happens through five/six-membered metallacycle through concerted metallation deprotonation. Further functionalization leads to C-N formation in the presence of an amidating reagent dioxazolone. Dioxazolone a robust and efficient amidating reagent has been utilized for the C-N bond formation reaction. The strategy has been applied for the azobenzene derivatives for further benzotriazole heterocycle synthesis. The 7-amino indoline derivatives have been synthesized at the ambient condition which endures an application in bioactive molecules. Subsequently, the amidated 2-amido aldehydes and ketones derivatives have been utilized for the synthesis of quindolinone alkaloids
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ZHAO, YIGANG. "Reduction of Tertiary Benzamides to Benzaldehydes by an in situ-Generated Schwartz Reagent (Cp2Zr(H)Cl); Formal Synthesis of Lysergic Acid 2. Ru-Catalyzed Amide-Directed Aryl C-H, C-N and C-O Bond Functionalizations: C-B Formation, C-C Suzuki Cross Coupling and Hydrodemethoxylation." Thesis, 2010. http://hdl.handle.net/1974/6671.

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Chapter 2 of the thesis describes a highly efficient in situ method for the reduction of amides to aldehydes and aryl O-carbamates to phenols and other transformations involving hydrozirconations. The method, as a three-component-type reaction, involves in situ generation of the Schwartz reagent (Cp2Zr(H)Cl) from Cp2ZrCl2 and the reductant, LiAlH(O-t-Bu)3, and immediate reaction with a substrate. Substrates include aliphatic and aromatic tertiary amides which are reduced to aldehydes, aryl O-carbamates which are reduced to phenols, and alkynes which undergo other transformations via hydrozirconation. Compared to prior methods, this method has advantage in that reagents are inexpensive and stable, reaction times are short, and reaction temperatures are generally conveniently at room temperature. The use of the in situ method described herein instead of the requirement for the synthesis of the commercially available Schwartz reagent is estimated to provide more than 50% reduction in cost. Chapter 3 of the thesis describes the discovery and development of efficient and regioselective Ru-catalyzed amide-directed C-H, C-N, C-O activation/C-C bond forming reactions, ester-directed C-O activation/C-C bond forming reaction, and amide-directed C-O activation/hydrodemethoxylation reactions under a simple RuH2(CO)(PPh3)3/toluene catalytic system. Of these, the amide-directed C-H activation/cross coupling reaction proceeds well but uniquely on furan 3-amide substrates while the ester-directed C-O activation is effective on the 2-MeO-1-naphthoic acid methyl ester. On the other hand, the amide-directed C-N and C-O activation/coupling reactions are broadly applicable on benzamides and naphthamides. All of these achievements of directed C-H, C-N, C-O activation/coupling reactions complement and may supercede the DoM (directed ortho metalation)-cross coupling strategy, and establish the catalytic base-free DoM-cross coupling process at non-cryogenic temperature as a convenient, economical and green alternative. The new catalytic amide-directed ortho-hydrodemethoxylation reaction has potential value in links to aromatic electrophilic substitution and DoM chemistries. Furthermore, a new borylation reaction via Ru-catalyzed amide-directed C-H activation/C-B bond forming process is also reported herein.
Thesis (Ph.D, Chemistry) -- Queen's University, 2010-12-21 11:12:35.564
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Book chapters on the topic "Indoline, aldehyde and C-H activation"

1

Taber, Douglass F. "Heteroaromatic Construction: The Li Synthesis of Mycoleptodiscin A." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0068.

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Kyungsoo Oh of Chung-Ang University cyclized (Org. Lett. 2015, 17, 450) the chloro enone 1 with NBS to the furan 2. Hongwei Zhou of Zhejiang University acylated (Adv. Synth. Catal. 2015, 357, 389) the imine 3, leading to the furan 4. H. Surya Prakash Rao of Pondicherry University found (Synlett 2014, 26, 1059) that under Blaise conditions, exposure of 5 to three equivalents of 6 led to the pyrrole 7. Yoshiaki Nishibayashi of the University of Tokyo and Yoshihiro Miyake, now at Nagoya University, prepared (Chem. Commun. 2014, 50, 8900) the pyrrole 10 by adding the silane 9 to the enone 8. Barry M. Trost of Stanford University developed (Org. Lett. 2015, 17, 1433) the phosphine-mediated cyclization of 11 to an intermediate that on brief exposure to a Pd catalyst was converted to the pyridine 12. Nagatoshi Nishiwaki of the Kochi University of Technology added (Chem. Lett. 2015, 44, 776) the dinitrolactam 14 to the enone 13 to give the pyridine 15. Metin Balci of the Middle East Technical University assembled (Org. Lett. 2015, 17, 964) the tricyclic pyridine 18 by adding propargyl amine 17 to the aldehyde 16. Chada Raji Reddy of the Indian Institute of Chemical Technology cyclized (Org. Lett. 2015, 17, 896) the azido enyne 19 to the pyridine 20 by simple exposure to I2. Björn C. G. Söderberg of West Virginia University used (J. Org. Chem. 2015, 80, 4783) a Pd catalyst to simultaneously reduce and cyclize 21 to the indole 22. Ranjan Jana of the Indian Institute of Chemical Biology effected (Org. Lett. 2015, 17, 672) sequential ortho C–H activation and cyclization, adding 23 to 24 to give the 2-substituted indole 25. In a complementary approach, Debabrata Maiti of the Indian Institute of Technology Bombay added (Chem. Eur. J. 2015, 21, 8723) 27 to 26 to give the 3-substituted indole 28. In a Type 8 construction, Nobutaka Fujii and Hiroaki Ohno of Kyoto University employed (Chem. Eur. J. 2015, 21, 1463) a gold catalyst to add 30 to 29, leading to 31.
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MacMillan, D. W. C., and A. J. B. Watson. "Aldol Processes with Aldehyde Donors." In Stereoselective Pericyclic Reactions, Cross Coupling, and C—H and C—X Activation, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-203-00425.

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3

Taber, Douglass. "C-H Functionalization to Form C-O, C-N, and C-C Bonds." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0015.

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A classic example of C-H functionalization is the familiar NBS bromination of a benzylic site. Recent updates of this approach allow for direct alkoxylation (J. Am. Chem. Soc. 2008, 130, 7824) and net amination (Organic Lett. 2008, 10, 1863). For the amination of simple aliphatic H’s, Holger F. Bettinger of Ruhr-Universität Bochum developed (Angew. Chem. Int. Ed. 2008, 47, 4744) the boryl azide 2. The insertion with 1 proceeded to give a statistical mixture of the nitrene insertion products 3 and 4. The tethered C-H functionalization devised (J. Am. Chem. Soc. 2008, 130, 7247) by Phil S. Baran of Scripps-La Jolla is selective, as in the conversion to 5 to 6, but appears to be limited to tertiary and benzylic C-H sites. Michael P. Doyle of the University of Maryland established (J. Org. Chem. 2008, 73, 4317) an elegant protocol for the oxidation of an alkyne such as 7 to the ynone 8. Note that the oxidation did not move the alkyne. Marta Catellani of the Università di Parma reported (Adv. Synth. Cat. 2008, 350, 565) the intriguing Pd-catalyzed conversion of 9 to 10. Under mild conditions, it might likely be possible to hydrolyze the vinyl ether to reveal the phenol 11. Another way of looking at this overall transformation would be to consider the ether 10 to be a protected form of the aldehyde 12. C-H activation can also lead to C-C bond formation. Irena S. Akhrem of the Nesmeyanov Institute, Moscow, described (Tetrahedron Lett. 2008, 49, 1399) a hydride-abstraction protocol for three-component coupling of a hydrocarbon 13 , an amine 14 , and CO, leading to the homologated amide 15. Hua Fu of Tsinghua University, Beijing, showed (J. Org. Chem. 2008 , 73, 3961) that oxidation of an amine 16 led to an intermediate that could be coupled with an alkyne 17 to give the propargylic amine 18. Products 15 and 18 are the result of sp2 and sp coupling, respectively. C-H functionalization leading to sp3 -sp3 coupling is less common. Jin-Quan Yu of Scripps/La Jolla found (J. Am. Chem. Soc. 2008, 130, 7190) that activation of the N-methoxy amide 19 in the presence of the alkyl boronic acid 20 gave smooth coupling, to 21.
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