<i>tert</i>-Butyl Hydroperoxide (TBHP)-Initiated Vicinal Sulfonamination of Alkynes: A Radical Annulation toward 3-Sulfonylindoles

Chen, Fei; Meng, Qingxi; Han, Shang-Qing; Han, Bing

doi:10.1021/acs.orglett.6b01427

Cited by 82 publications

(32 citation statements)

References 67 publications

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“…A facile vicinal sulfonamination of alkynes by the reaction of accessible 2‐alkynylaryl azides with sulfinic acids in the presence of TBHP was developed recently . The sulfonyl radical adds to the alkynyl moiety, then the intramolecular cyclization of the alkenyl radical with an azido group happens.…”

Section: Radical‐mediated Reactionsmentioning

confidence: 99%

Recent Advances in Reactions of Azides

2017

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Azides are important intermediates in organic synthesis. They can function as precursors to form amines, amides, quinolones, pyridines, triazoles, amidines, indoles, and so on. Although there are some reviews about the applications of azides, few are concerned about their fundamental mechanisms. This review will focus on recent advances of azides based on three reactivity patterns, which may enlighten the further research.

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Section: Radical‐mediated Reactionsmentioning

confidence: 99%

Recent Advances in Reactions of Azides

2017

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“…Heterocyclic substituted substrate such as 1 p can also deliver the corresponding product 3 pa in 60% yield. Unfortunately, aliphatic alkynyls such as 1 q and 1 r (R=hexyl and trimethylsilyl) cannot deliver the corresponding products 3 qa and 3 ra , with the recovery of substrates, maybe due to the relatively lower stability of the correspondingly generated alkyl substituted alkenyl radicals [9] . Additionally, the reaction can scale up to 1 mmol without the loss of efficiency to deliver 3 aa in 81% yield.…”

Section: Figurementioning

confidence: 99%

Three‐Component Vicinal Sulfonamination of Alkynes toward 3‐Sulfonylindoles via the Insertion of Sulfur Dioxide

Zhang²,

Chen³

et al. 2021

Asian J Org Chem

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A convenient and efficient three‐component transformation of 2‐alkynyl arylazides, aryldiazonium tetrafluoroborates and sodium metabisulfite has been developed under mild and transition‐metal‐free conditions. Sodium metabisulfite which is cheap, easily available and abundant in nature is successfully utilized as SO2 surrogate, leading to a series of 3‐sulfonylindole derivatives in moderate to good yields. Cascade radical addition/cyclization was involved in this protocol with the formation of two C−S bonds and one C−N bond in one‐pot.

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“…In the first case, the reaction proceeded under the action of the I 2 /TBHP system in ethyl acetate at 80 °C under air (Scheme 199a) [246] . In the second one, catalytic amount of TBHP, DMF as the solvent, 80 °C and an inert atmosphere were necessary (Scheme 199b) [247] . The key steps of both these transformations are the addition of the sulfonyl radical to the triple bond to form the vinyl radical and subsequent intramolecular cyclization.…”

Section: Sulfonylation Followed By Cyclizationmentioning

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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tert-Butyl Hydroperoxide (TBHP)-Initiated Vicinal Sulfonamination of Alkynes: A Radical Annulation toward 3-Sulfonylindoles

Cited by 82 publications

References 67 publications

Recent Advances in Reactions of Azides

Recent Advances in Reactions of Azides

Three‐Component Vicinal Sulfonamination of Alkynes toward 3‐Sulfonylindoles via the Insertion of Sulfur Dioxide

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

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