Issue 16, 2024

Nickel-catalyzed arylative cyclization of 1,6-enynes: arylation of unactivated alkene moieties

Abstract

We developed catalytic cyclization of 1,6-enynes, whereby an aryl group is introduced at an unactivated alkene moiety. The reaction of a 1,6-enyne with an arylboronic acid in the presence of an Ni(cod)2/P(4-MeOC6H4)3 complex yields a five-membered ring product incorporating an all-carbon quaternary center. Experimental studies and extensive DFT calculations reveal that an Ni(I) species is involved in the catalytic cycle, which is an uncommon pathway involving transmetalation, oxidative cyclization, selective sp3–sp2 carbon–carbon bond formation, and finally hydrolysis.

Graphical abstract: Nickel-catalyzed arylative cyclization of 1,6-enynes: arylation of unactivated alkene moieties

Supplementary files

Article information

Article type
Research Article
Submitted
03 May 2024
Accepted
23 Jun 2024
First published
25 Jun 2024

Org. Chem. Front., 2024,11, 4487-4495

Nickel-catalyzed arylative cyclization of 1,6-enynes: arylation of unactivated alkene moieties

J. Gao, Q. Wei, Z. Zhang, Z. Su, J. Ming and Y. Zhang, Org. Chem. Front., 2024, 11, 4487 DOI: 10.1039/D4QO00784K

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