Nickel-Catalyzed Stereoselective Cascade C–F Functionalizations of <i>gem</i>-Difluoroalkenes
Xiaowei Li, Yuxiu Li, Zemin Wang, Wenlong Shan, Ruihua Liu, Cong Shi, Hongyun Qin, Leifeng Yuan, Xiangqian Li, Dayong Shi
Abstract
The activation and functionalization of C–F bonds for the construction of C–C and C–X bonds have drawn significant research attention in recent years. However, the chemo- and stereoselective control of dual C–F bond functionalization of gem -difluoroalkenes remains a formidable challenge. Herein, a Ni-catalyzed reductive cross-coupling of gem -difluoroalkenes with alkenyl-electrophiles and D 2 O that allowed the generation of C(sp 2 )–C(sp 2 ) bonds and C(sp 2 )–D bonds in one pot by successive defluorination is described. This methodology offers facile access to various deuterated 1,3-dienes with broad functional group compatibility and ( E )-selectivity under mild conditions. Preliminary mechanistic studies indicate that α-alkenyl-substituted monofluoroalkenes might be intermediates in this protocol.