Copper‐Catalyzed Radical Sulfonylation of <i>N</i>‐Propargylindoles with Concomitant 1,2‐Aryl Migration

Zhu, Xinyu; Han, Yong-Jun; Li, Ming; Li, Xue‐Song; Liang, Yong‐Min

doi:10.1002/adsc.201800414

Cited by 29 publications

(9 citation statements)

References 48 publications

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“…The Liang group provided a radical sulfonylation of 2‐aryl‐ N ‐propargylindole to yield pyrrolo[1,2‐α]indole derivatives by 1,2‐aryl migration and C−S/C−C/C=O bonds formation (Eq. 30‐1).…”

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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“…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). [257] The oxidative spirocyclization of arylpropiolamides 472 into azaspiro [4,5]trienones 475 proceeded with sulfonyl hydrazides 473 or sulfinic acids 474 with the use of the I 2 O 5 /TBHP oxidative system in dioxane at 80°C [258] or under visible light irradiation (photocatalyst -eosin Y) in MeCNÀ H 2 O at room temperature [259] (Scheme 207). The reaction includes the formation of the sulfonyl radical under oxidative conditions, its addition to the triple bond, ipso- carbocyclization, dearomatization, hydratation, and oxidation.…”

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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“…Phenyl sulfonyl hydrazines gave moderate yields while heteroaryl sulfonyl hydrazines were not favorable for this conversion. In 2018, the Liang group developed a novel protocol for the synthesis of 2-sulfonated pyrrolo[1,2-a]indoles using toluenesulfonyl hydrazide as a sulfonyl reagent (Scheme 50) [72]. N-propargyl-substituted indoles were used as substrates and the reaction occurred in the presence of Cu(NO 3 ) 2 •3H 2 O as catalyst, TBHP and AgTFA in DCE at 90 • C. Toluenesulfonyl hydrazide proved as a good tosyl source while sodium tosylate and tosyl chloride were not able to furnish this conversion under the standard condition.…”

Section: Scheme 48mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Zhang

Ding

et al. 2020

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The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have emerged as an important strategy to construct C-S bonds. In this review, we focus on the recent advances on the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates involving C-S bond construction.

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Copper‐Catalyzed Radical Sulfonylation of N‐Propargylindoles with Concomitant 1,2‐Aryl Migration

Cited by 29 publications

References 48 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

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

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

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