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Metal-free hydrosulfonylation of α,β-unsaturated ketones: synthesis and application of γ-keto sulfones.

ABSTRACT: γ-Keto sulfones are versatile building blocks and valuable intermediates in organic synthesis and pharmaceutical chemistry. Motivated by their excellent properties, we herein report a green, convenient, metal-free hydrosulfonylation method for a variety of ynones, vinyl ketones, and sodium sulfinates in the absence of stoichiometric oxidants. This operationally simple protocol provides straightforward and practical access to a wide range of γ-keto sulfones with broad functional group tolerance from easily available starting materials. Moreover, the β,γ-unsaturated keto sulfones could further react with 2,3-butadienoate to generate cyclopentenes in phosphine-mediated [3 + 2] cycloaddition.

SUBMITTER: Cheng X

PROVIDER: S-EPMC9745886 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Metal-free hydrosulfonylation of α,β-unsaturated ketones: synthesis and application of γ-keto sulfones.

Cheng Xiufang X Wang Shuo S Wei Yibo Y Wang Huamin H Lin Ying-Wu YW

RSC advances 20221213 55

γ-Keto sulfones are versatile building blocks and valuable intermediates in organic synthesis and pharmaceutical chemistry. Motivated by their excellent properties, we herein report a green, convenient, metal-free hydrosulfonylation method for a variety of ynones, vinyl ketones, and sodium sulfinates in the absence of stoichiometric oxidants. This operationally simple protocol provides straightforward and practical access to a wide range of γ-keto sulfones with broad functional group tolerance f ...[more]

PMID: 36545103

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