Direct synthesis of α-functionalized amides via heteroatom–hydrogen insertion reactions using amide-sulfoxonium ylides

Haiting Wu, Yougen Xu, An Lin, Zhi Wang, Huanjun Chen, Xinwei Zhu, Yadong Gao () and Lebin Su ()
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Haiting Wu: Bioland Laboratory
Yougen Xu: Bioland Laboratory
An Lin: Bioland Laboratory
Zhi Wang: Chinese Academy of Medical Sciences & Peking Union Medical College
Huanjun Chen: Bioland Laboratory
Xinwei Zhu: Bioland Laboratory
Yadong Gao: Chinese Academy of Medical Sciences & Peking Union Medical College
Lebin Su: Bioland Laboratory

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract α-Functionalized Si-, Ge-, B-, Se-, and S-amide moieties are present in many medicinally active molecules, but their synthesis remains challenging. Here, we demonstrate a high-throughput synthesis using amide-sulfoxonium ylides as carbene precursors in a Si–H, Ge–H, B–H, Se–H, and S–H insertion reactions to target a wide range of α-silyl, α-geryl, α-boryl, α-selenyl, and α-sulfur (hetero)amides. The process is featured as simple operation, mild conditions, broad substrate scope, high functional group compatibility, and excellent chemoselectivity. Both experimental and computational studies are conducted to explore the mechanisms underlying the formation of C–Si/Ge/B/Se/S bond. This research highlights the use of highly selective X–H insertion reactions with amide-sulfoxonium ylide-derived carbenes, paving the way for the preparation of diverse functional organosilane, organogermane, organoboron, organoselenium, and organosulfur compounds from accessible and bench-stable precursors.

Date: 2024
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DOI: 10.1038/s41467-024-54532-3

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