A Titanium-Catalyzed Reductive α-Desulfonylation.

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. © 2021 The Authors. Published by Wiley-VCH GmbH.

Citation

Christoph Kern, Jan Selau, Jan Streuff. A Titanium-Catalyzed Reductive α-Desulfonylation. Chemistry (Weinheim an der Bergstrasse, Germany). 2021 Apr 07;27(20):6178-6182

PMID: 33539578

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