Abstract:
:Transition metal-catalyzed enantioselective Sonogashira-type oxidative C(sp3)-C(sp) coupling of unactivated C(sp3)-H bonds with terminal alkynes has remained a prominent challenge. The difficulties mainly stem from the regiocontrol in unactivated C(sp3)-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(sp3)-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(sp3)-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(sp3)-C(sp), C(sp3)-C(sp2), and C(sp3)-C(sp3) bonds when allied with follow-up transformations.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Zhang ZH,Dong XY,Du XY,Gu QS,Li ZL,Liu XYdoi
10.1038/s41467-019-13705-1subject
Has Abstractpub_date
2019-12-12 00:00:00pages
5689issue
1issn
2041-1723pii
10.1038/s41467-019-13705-1journal_volume
10pub_type
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