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Divergent reactivity of divinylsilanes toward sulfonamides in different oxidative systems.

ABSTRACT: Oxidative sulfonamidation of divinylsilanes with various sulfonamides in different solvents is reported. With t-BuOI as an oxidant, halogenation is the main process, whereas aziridines are the minor products. With NBS in CH₂Cl₂ the products of bromination or bromosulfonamidation were obtained, whereas in MeCN or THF the Ritter-type solvent interception products are formed. The obtained bromosulfonamidation products undergo base-induced cyclization to various heterocycles, including imidazolines, 1,4-oxazocanes, or Si,N-containing heterocycles of a new type, 1,3,5-diazasilinanes, in up to quantitative yield.

SUBMITTER: Moskalik MY

PROVIDER: S-EPMC9057569 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Divergent reactivity of divinylsilanes toward sulfonamides in different oxidative systems.

Moskalik Mikhail Yu MY Astakhova Vera V VV Shainyan Bagrat A BA

RSC advances 20201106 66

Oxidative sulfonamidation of divinylsilanes with various sulfonamides in different solvents is reported. With t-BuOI as an oxidant, halogenation is the main process, whereas aziridines are the minor products. With NBS in CH2Cl2 the products of bromination or bromosulfonamidation were obtained, whereas in MeCN or THF the Ritter-type solvent interception products are formed. The obtained bromosulfonamidation products undergo base-induced cyclization to various heterocy ...[more]

PMID: 35520841

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