Copper-Catalyzed Oxidative Cyclization of Alkynes with Sulfonylhydrazides Leading to 2-Sulfonated 9<i>H</i>-pyrrolo[1,2-<i>a</i>]indol-9-ones

Zhu, Xinyu; Li, Ming; Han, Yong-Jun; Chen, Si; Li, Xuesong; Liang, Yong‐Min

doi:10.1021/acs.joc.7b01497

Cited by 48 publications

(18 citation statements)

References 56 publications

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“…The Liang group reported that the cascade of sulfonylation, cyclization, O‐addition, oxidation was able to achieve the construction of 2‐sulfonyl pyrrolo[1,2‐a]indol‐9‐ones (Eq. 28‐1).…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…In 2017, Liang group disclosed a CuCl 2 . 2H 2 O‐catalyzed tandem reaction of N ‐propargyl‐substituted indoles and sulfonylhydrazides for the synthesis of 2‐sulfonated 9 H ‐pyrrolo[1,2‐a]indol‐9‐ones with an assistance of TBHP (Scheme ) . In this work, the authors found that TBHP were necessary for this reaction.…”

Section: Additive Effect On the Tandem Reactionmentioning

confidence: 93%

Additive Effects on Copper‐Catalyzed Tandem Reactions

Wu¹,

Ma²,

Xie

2019

Asian J Org Chem

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Introduction of a suitable additive to coppercatalyzed tandem reactions during heterocyclic synthesis is an efficient strategy. This short review mainly describes the results obtained over the period of January 2014 to December 2018 in the area of copper-catalyzed intramolecular tandem reactions to synthesize heterocyclic compounds.Five types of additives that can be used to improve reactivity and selectivity of these tandem reactions were highlighted. Particular attention is paid to demonstrate the importance of additives by comparing results obtained in its absence and presence, and the probable mechanistic role of the additive is discussed based on original articles. . Cu(MeCN) 4 PF 4 -catalyzed reaction of 1,n-enynes and α-carbonyl alkyl bromides. Scheme 33. Cu(OTf) 2 -catalyzed reaction of amino acids and 2-benzoylquinolines. Scheme 34. CuI-catalyzed reaction of o-iodoaniline derivatives S 8 and Ntosylhydrazone. 2 3 4 5 6 7 8

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“…The formation of 9H- Using the CuCl 2 • 2H 2 O/TBHP/AcOH system, 9Hpyrrolo[1,2-a]indol-9-ones (fluorazones) 468 were obtained from N-propargyl indoles 466 and aryl and hetarylsulfonyl hydrazides 467 (Scheme 205). [256] The synthesis of 1H-pyrrolo[1,2-a]indoles 471 using 2-aryl N-propargyl indoles 469 and aromatic sulfonyl hydrazides 470 under the action of the Cu(NO 3 ) 2 • 3H 2 O/ TBHP/AgTFA system was performed in DCE at 90°C under air. During this transformation, CÀ S, CÀ C, and C=O bonds are constructed and 1,2-migration of the aryl fragment takes place (Scheme 206).…”

Section: Construction Of Five-membered Heterocyclesmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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Copper-Catalyzed Oxidative Cyclization of Alkynes with Sulfonylhydrazides Leading to 2-Sulfonated 9H-pyrrolo[1,2-a]indol-9-ones

Cited by 48 publications

References 56 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Additive Effects on Copper‐Catalyzed Tandem Reactions

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

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