Nickel-Catalyzed Stereoselective Alkenylation of C(sp3)-H Bonds with Terminal Alkynes.

A nickel-catalyzed stereoselective alkenylation of an unactivated β-C(sp3)-H bond in aliphatic amide with terminal alkynes using 8-aminoquinoline auxiliary is reported for the first time. This reaction displays excellent functional group tolerance with respect to both aliphatic amides and terminal alkynes and features a cheap nickel catalytic system. The 8-aminoquinolyl directing group could be smoothly removed, and the resultant β-styrylcarboxylic acid derivatives could serve as versatile building blocks for further transformation.