Copper-Catalyzed Umpolung of Imines through Carbon-to-Nitrogen Boryl Migration

• Published in: ACS catalysis Vol. 9; no. 5; pp. 4388 - 4393
• Main Authors: Li, Zhenghua, Zhang, Liang, Nishiura, Masayoshi, Hou, Zhaomin
• Format: Journal Article
• Language: English
• Published: American Chemical Society 03.05.2019
• Subjects: copper catalysis; amine synthesis; imine umpolung; allylation; boryl migration

We report a general strategy for the catalytic umpolung of imines, which was enabled by an unprecedented 1,2-boryl carbon-to-nitrogen migration. Based on the discovery of a rearrangement of an α-borylalkylamido copper intermediate to an α-borylaminoalkyl copper species through 1,2-migration of a bor...