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Transition metal-catalyzed enantioselective Sonogashira-type oxidative C( sp  3 )—C( sp ) coupling of unactivated C( sp  3 )−H bonds with terminal alkynes has remained a prominent challenge. The difficulties mainly stem from the regiocontrol in unactivated C( sp  3 )—H bond functionalization and the inhibition of readily occurring Glaser homocoupling of terminal alkynes. Here, we report a copper/chiral cinchona alkaloid-based  N,N,P -ligand catalyst for asymmetric oxidative cross-coupling of unactivated C( sp  3 )—H bonds with terminal alkynes in a highly regio-, chemo-, and enantioselective manner. The use of  N -fluoroamide as a mild oxidant is essential to site-selectively generate alkyl radical species while efficiently avoiding Glaser homocoupling. This reaction accommodates a range of (hetero)aryl and alkyl alkynes; (hetero)benzylic and propargylic C( sp  3 )−H bonds are all applicable. This process allows expedient access to chiral alkynyl amides/aldehydes. More importantly, it also provides a versatile tool for the construction of chiral C( sp  3 )—C( sp ), C( sp  3 )—C( sp  2 ), and C( sp  3 )—C( sp  3 ) bonds when allied with follow-up transformations.

Copper-catalyzed enantioselective Sonogashira-type oxidative cross-coupling of unactivated C(sp3)−H bonds with alkynes