Regioselective C₃Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1846 - 1857

Published: Jan. 12, 2024

Herein, we describe an efficient transition-metal-free regioselective C3alkylation of indoles for the synthesis bis(indolyl)methanes and 3-styryl indoles. Nitrobenzene is employed as oxidant to oxidize alcohols in presence a strong base reaction avoids use transition metals such Ru Mn. The protocol provides favorable route access biologically active compounds arundine, vibrindole A, turbomycin B.

Language: Английский

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Recent advances in hydride transfer-involved C(sp³)–H activation reactions

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(6), P. 1364 - 1383

Published: Jan. 1, 2021

This review summarizes the recent progresses (2016–2020) in hydride transfer-enabled C(sp³)–H activation according to reaction types, categorized into intramolecular/intermolecular functionalization, and reduction.

Language: Английский

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Tris(pentafluorophenyl)borane catalyzed C–C and C–heteroatom bond formation

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(6), P. 1230 - 1267

Published: Jan. 1, 2021

This review showcases a collective depiction on the potential utility of BCF as versatile catalyst to develop various synthetic transformations.

Language: Английский

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Electron-deficient boron-based catalysts for C–H bond functionalisation

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 50(3), P. 1945 - 1967

Published: Dec. 16, 2020

In contrast to transition metal-catalysed C-H functionalisation, highly efficient construction of C-C and C-X (X = N, O, S, B, Si, etc.) bonds through metal-free catalytic functionalisation remains one the most challenging tasks for synthetic chemists. recent years, electron-deficient boron-based catalyst systems have exhibited great potential bond transformations. Such emerging may greatly enrich chemistry main-group element catalysis, will also provide enormous opportunities in chemistry, materials chemical biology. This article aims give a timely comprehensive overview recognise current status catalysis stimulate development more systems.

Language: Английский

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Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(6), P. 3720 - 3737

Published: Jan. 1, 2021

Borane mediated hydride abstraction of amines efficiently generates useful iminium salts. This review explores this fascinating reactivity and discusses how the intermediates are utilised in a variety stoichiometric catalytic processes.

Language: Английский

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Recent advances in the functionalization of saturated cyclic amines

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(16), P. 4582 - 4606

Published: Jan. 1, 2021

Functionalized cyclic amines are the essential structural moieties of numerous biologically active compounds. This review summarized most recent advances in C–H, C–N and C–C bond functionalization saturated amines.

Language: Английский

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A photoredox-catalyzed approach for formal hydride abstraction to enable C –H functionalization with nucleophilic partners (F, C, O, N, and Br/Cl)

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(2), P. 292 - 308

Published: Jan. 19, 2022

Language: Английский

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Recent Advances in Indole Synthesis and the Related Alkylation

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(6)

Published: May 2, 2023

Abstract The derivatives of indoles are very useful intermediates in pharmaceuticals and organic synthesis. efficient synthesis the indole blocks related functionalizations, especially alkylation hot topics recent years. This review will focus on following two aspects: i) new developments for which was catalyzed by transition metals, indoles, including one N 1 ‐position, C 2 as well 3 ‐position. 1. Introduction 2. Synthesis various metals 2.1. palladium catalysts 2.2. other metal 3. Alkylation 3.1. ‐alkylation 3.2. 3.3.

Language: Английский

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B(C₆F₅)₃-Catalyzed Dehydrogenation of Pyrrolidines to Form Pyrroles

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 4856 - 4864

Published: March 18, 2024

Pyrroles are important N-heterocycles found in medicines and materials. The formation of pyrroles from widely accessible pyrrolidines is a potentially attractive strategy but an underdeveloped approach due to the sensitivity oxidative conditions required achieve such transformation. Herein, we report catalytic that employs commercially available B(C6F5)3 operationally simple procedure allows serve as direct synthons for pyrroles. Mechanistic studies have revealed insights into borane-catalyzed dehydrogenative processes.

Language: Английский

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Direct Conversion of N-Alkylamines to N-Propargylamines through C–H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(38), P. 16493 - 16505

Published: Aug. 24, 2020

An efficient catalytic method to convert an α-C–H bond of N-alkylamines into α-C–alkynyl was developed. In the past, such transformations were carried out under oxidative conditions, and enantioselective variants confined tetrahydroisoquinoline derivatives. Here, we disclose a for union trimethylsilyl alkynes, without presence external oxidant promoted through cooperative actions two Lewis acids, B(C6F5)3 Cu-based complex. A variety propargylamines can be synthesized in high diastereo- enantioselectivity. The utility approach is demonstrated by late-stage site-selective modification bioactive amines. Kinetic investigations that shed light on various mechanistic nuances process are presented.

Language: Английский

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