Photoinduced Chemo-, Site- and Stereoselective α-C(sp3 )-H Functionalization of Sulfides.

Zhenda Tan, Shibo Zhu, Yangbin Liu, Xiaoming Feng

Angewandte Chemie (International ed. in English) 2022 Jul 18

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The ubiquity of sulfur-containing molecules in biologically active natural products and pharmaceuticals has long attracted synthetic chemists to develop efficient strategies towards their synthesis. The strategy of direct α-C(sp3 )-H modification of sulfides provides a streamlining access to complex sulfur-containing molecules. Herein, we report a photoinduced chemo-, site- and stereoselective α-C(sp3 )-H functionalization of sulfides using isatins as the photoredox reagent and coupling partner catalyzed by a chiral gallium(III)-N,N'-dioxide complex. The reaction proceeds through a verified single-electron transfer (SET) mechanism with high efficiency, excellent functional group tolerance, as well as a broad substrate scope. Importantly, this cross-coupling protocol is highly selective for the direct late-stage functionalization of methionine-related peptides, regardless of the inherent structural similarity and complexity of diverse residues. © 2022 Wiley-VCH GmbH.

Citation

Zhenda Tan, Shibo Zhu, Yangbin Liu, Xiaoming Feng. Photoinduced Chemo-, Site- and Stereoselective α-C(sp3 )-H Functionalization of Sulfides. Angewandte Chemie (International ed. in English). 2022 Jul 18;61(29):e202203374