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A Titanium-Catalyzed Reductive α-Desulfonylation.

ABSTRACT: A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst-dependent mechanism involving a homolytic C-S cleavage.

SUBMITTER: Kern C

PROVIDER: S-EPMC8048938 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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A Titanium-Catalyzed Reductive α-Desulfonylation.

Kern Christoph C Selau Jan J Streuff Jan J

Chemistry (Weinheim an der Bergstrasse, Germany) 20210305 20

A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalys ...[more]

PMID: 33539578

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