B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Regioselective Deuteration of Terminal Olefins Using D<sub>2</sub>O as the Deuterium Source
Jinfeng Zheng, Jian‐Fei Bai, Yun Jia, Tao Qian, Jianbo Tang, Zhi‐Jiang Jiang, Jia Chen, Zhanghua Gao
Abstract
The selective deuteration of α-alkyl olefins is challenging due to their polymerization tendency and limited catalytic options. Herein, we report the B(C 6 F 5 ) 3 -catalyzed deuteration of terminal olefins using D 2 O as the deuterium source. This approach efficiently achieves hydrogen–deuterium exchange via carbocation intermediates, demonstrating broad substrate scope, including α-methylstyrenes, internal alkenes, heterocycles, and natural product derivatives, with high deuterium incorporation and functional group tolerance. Additionally, optimized conditions enable the synthesis of fully deuterated oligomeric products, highlighting the method’s versatility.