α-Aminocarbene-Mediated Si-H Insertion: Deoxygenative Silylation of Aromatic Amides with Silanes

Jiwen Jiao, Wenhan Yang and Xiaoming Wang*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: xiaomingsioc.ac.cn

J. Jiao, W. Yang, X. Wang, J. Org. Chem., 2023, 88, 594-601.

DOI: 10.1021/acs.joc.2c02649

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Abstract

Sm/SmI₂ mediates the generation of α-aminocarbene intermediates from amide precursors for Pd-catalyzed Si-H insertion reactions to provide α-aminosilanes. This deoxygenative cross-coupling of amides and silanes offers simplicity and versatility.

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proposed mechanism

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Key Words

benzyl silanes, samarium

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ID: J42-Y2023