Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines

Chunyu Han; Xianhai Tian; Huili Zhang; Frank Rominger; A Stephen K Hashmi

doi:10.1021/acs.orglett.1c01486

Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp²)-H Alkynylation of Acceptor-Substituted Enamines

Org Lett. 2021 Jun 18;23(12):4764-4768. doi: 10.1021/acs.orglett.1c01486. Epub 2021 Jun 9.

Authors

Chunyu Han¹, Xianhai Tian¹, Huili Zhang¹, Frank Rominger¹, A Stephen K Hashmi^{1

2}

Affiliations

¹ Organisch Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
² Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia.

PMID: 34105968
DOI: 10.1021/acs.orglett.1c01486

Abstract

A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp²)-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.