Copper-Catalyzed Azidative Multifunctionalization of Alkynes

Zheng, Guangfan; Sun, Jiaqiong; Liu, Yang; Yang, Shengbiao; Li, Yan; Sun, Haizhu; Zhang, Qian

doi:10.1021/acs.joc.7b02148

Cited by 15 publications

(8 citation statements)

References 40 publications

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“…Based on these experimental results and literature precedents, , we propose the following tentative reaction mechanism. The transformation started with the oxidation of Cu(II) to Cu(III) complex by NFSI.…”

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confidence: 61%

“…In view of this above-mentioned synthetic gap and our interest in radical reactions, we hence decided to focus on the ketone synthesis from simple alkyne cleavage using earth-abundant copper catalysts . At the onset of our project, we noticed in the literature that the combination of copper catalyst and NFSI ( N -fluorobenzenesulfonimide) effectively enabled the addition of N -radicals to alkynes, and the resulting activated vinyl radical species upon aryl migration could afford a variety of multifunctionalized products . Notwithstanding such progress, we questioned whether incorporating extra oxidants could facilitate the cleavage of Cu/NFSI-activated alkyne intermediates to furnish the overall alkyne cleavage products.…”

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confidence: 99%

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Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones

et al. 2020

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A copper-catalyzed oxidative cleavage reaction of alkynes using NFSI and TBHP was described. Various terminal and internal alkyne substrates were employed to render quick access to aryl ketone products in moderate to good yields. NFSI not only functioned as N-centered radical precursors but also engaged in the aryl group migration. Mechanistic studies also suggested the important role of water in the title reactions.

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confidence: 61%

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confidence: 99%

Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones

et al. 2020

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“…In the course of their endeavors, Zhang et al. discovered that imines 135 - 5 could be obtained in good yields when the mixture of simple internal alkyne 135 - 1 , NFSI, and TMSN 3 was exposed to 5 mol % of CuCl and 5 mol % of N-containing bidentate Phen in DCE at 70 °C (Scheme A) . Mechanistic investigation showed that the in situ generated α-aryl-α-imino carbon radical 135 - 11 will recombine with Cu(II) species to yield organocopper(III) species 135 - 12 (Scheme B).…”

Section: Radical-mediated Desulfonylation Of N-containing Sulfonyl De...mentioning

confidence: 99%

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

et al. 2021

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As the "chemical chameleon", sulfonyl-containing compounds and their variants have been merged with various types of reactions for the efficient construction of diverse molecular architectures by taking advantage of their incredible reactive flexibility. Currently, their involvement in radical transformations, in which the sulfonyl group typically acts as a leaving group via selective C−S, N−S, O−S, S−S, and Se−S bond cleavage/ functionalization, has facilitated new bond formation strategies which are complementary to classical two-electron cross-couplings via organometallic or ionic intermediates. Considering the great influence and synthetic potential of these novel avenues, we summarize recent advances in this rapidly expanding area by discussing the reaction designs, substrate scopes, mechanistic studies, and their limitations, outlining the state-of-the-art processes involved in radical-mediated desulfonylation and related transformations. With a specific emphasis on their synthetic applications, we believe this review will be useful for medicinal and synthetic organic chemists who are interested in radical chemistry and radical-mediated desulfonylation in particular. CONTENTS

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“…Zheng et al [21] . described a facile and efficient copper‐catalyzed azidative multifunctionalization of various internal alkyne 42 by using of NFSI ( N ‐fluorobenzene sulphonimide) and TMSN 3.…”

Section: Synthesis Of Fused 123‐triazolesmentioning

confidence: 99%

Progress in the Synthesis of Fused 1,2,3‐Triazoles

et al. 2021

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Fused heterocycles display prodigious prominence in diverse field ranging from medicinal chemistry to material science and chemical biology to catalysis. Owing to biological importance, fused 1,2,3‐triazoles have gained much attention and hence, enormous efforts on its synthesis is given by the chemists. Diverse functionalized fused polycyclic 1,2,3‐triazole heterocycles have been designed using Huisgen's thermal intramolecular cycloaddition, copper catalyzed cycloaddition, bimetallic catalytic, greener and other miscellaneous approaches. Novel methodologies that use modified substrates such as ketones, enals, β‐keto esters, olefins, enones, C−H acids etc. in place of alkynes have been developed. Herein, synthetic methodologies to construct fused 1,2,3‐triazoles are briefly discussed.

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Copper-Catalyzed Azidative Multifunctionalization of Alkynes

Cited by 15 publications

References 40 publications

Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones

Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

Progress in the Synthesis of Fused 1,2,3‐Triazoles

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