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Photoinduced C(sp3)-H sulfination empowers the direct and chemoselective introduction of the sulfonyl group.

ABSTRACT: Direct installation of the sulfinate group by the functionalization of unreactive aliphatic C-H bonds can provide access to most classes of organosulfur compounds, because of the central position of sulfinates as sulfonyl group linchpins. Despite the importance of the sulfonyl group in synthesis, medicine, and materials science, a direct C(sp3)-H sulfination reaction that can convert abundant aliphatic C-H bonds to sulfinates has remained elusive, due to the reactivity of sulfinates that are incompatible with typical oxidation-driven C-H functionalization approaches. We report herein a photoinduced C(sp3)-H sulfination reaction that is mediated by sodium metabisulfite and enables access to a variety of sulfinates. The reaction proceeds with high chemoselectivity and moderate to good regioselectivity, affording only monosulfination products and can be used for a solvent-controlled regiodivergent distal C(sp3)-H functionalization.

SUBMITTER: Jin S 

PROVIDER: S-EPMC8549786 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Photoinduced C(sp<sup>3</sup>)-H sulfination empowers the direct and chemoselective introduction of the sulfonyl group.

Jin Shengfei S   Haug Graham C GC   Trevino Ramon R   Nguyen Viet D VD   Arman Hadi D HD   Larionov Oleg V OV  

Chemical science 20210928 41

Direct installation of the sulfinate group by the functionalization of unreactive aliphatic C-H bonds can provide access to most classes of organosulfur compounds, because of the central position of sulfinates as sulfonyl group linchpins. Despite the importance of the sulfonyl group in synthesis, medicine, and materials science, a direct C(sp<sup>3</sup>)-H sulfination reaction that can convert abundant aliphatic C-H bonds to sulfinates has remained elusive, due to the reactivity of sulfinates t  ...[more]

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