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Benzyl thioether formation merging copper catalysis.

ABSTRACT: A novel copper-catalyzed thioetherification reaction has been developed to afford benzyl thioethers in moderate to excellent yields. Under the mild and easy-to-operate conditions, a variety of thioethers are efficiently prepared from readily available benzyl alcohols (primary, secondary, and tertiary) and thiols in the presence of Cu(OTf)2 as the Lewis acid catalysis. This C-S bond formation protocol furnishes exceptional chemoselectivity, and the preliminary mechanism studies show that the reaction should proceed through a Lewis-acid-mediated SN1-type nucleophilic attack of the carbocations formed in situ.

SUBMITTER: Xu B 

PROVIDER: S-EPMC8697992 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Benzyl thioether formation merging copper catalysis.

Xu Bing B   Lin Ying Y   Ye Yang Y   Xu Li L   Xie Tian T   Ye Xiang-Yang XY  

RSC advances 20211223 2

A novel copper-catalyzed thioetherification reaction has been developed to afford benzyl thioethers in moderate to excellent yields. Under the mild and easy-to-operate conditions, a variety of thioethers are efficiently prepared from readily available benzyl alcohols (primary, secondary, and tertiary) and thiols in the presence of Cu(OTf)<sub>2</sub> as the Lewis acid catalysis. This C-S bond formation protocol furnishes exceptional chemoselectivity, and the preliminary mechanism studies show th  ...[more]

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