Synthesis of α-Aminosilanes by 1,2-Metalate Rearrangement Deoxygenative Silylation of Aromatic Amides

Lu Zhou; Jian Qiu; Cece Wang; Feng Zhang; Kai Yang; Qiuling Song

doi:10.1021/acs.orglett.2c01041

Synthesis of α-Aminosilanes by 1,2-Metalate Rearrangement Deoxygenative Silylation of Aromatic Amides

Org Lett. 2022 May 6;24(17):3249-3253. doi: 10.1021/acs.orglett.2c01041. Epub 2022 Apr 27.

Authors

Lu Zhou¹, Jian Qiu¹, Cece Wang¹, Feng Zhang¹, Kai Yang¹, Qiuling Song^{1

2

3}

Affiliations

¹ Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian 350108, China.
² Institute of Next Generation Matter Transformation, College of Materials Science Engineering, Huaqiao University, Xiamen, Fujian 361021, China.
³ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

PMID: 35475726
DOI: 10.1021/acs.orglett.2c01041

Abstract

An efficient nickel-catalyzed deoxygenative silylation reaction of aromatic amides with silylboranes in the presence of a Sm/SmI₂ system for the construction of α-aminosilanes is described. This strategy provides a direct method for synthesizing α-aminosilanes with high efficiency and good functional group compatibility and includes readily accessible starting materials and valuable products.