Issue 2, 2016

A ligand-controlled switch of regioselectivity in ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents

Abstract

A ligand-controlled regioselectivity switch of ring-opening coupling reaction of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents providing differently substituted β-vinylic naphthalenes in moderate to excellent yields was reported: when Pd(OAc)2 was used, the aromatic group from the Grignard reagent regioselectively coupled to the naphthyl ring after the ring-opening of three-membered cycle, which is different from the Pd(PPh3)2Cl2-catalyzed reaction. Based on a careful NMR study, we concluded that it may be explained by the ligand effect.

Graphical abstract: A ligand-controlled switch of regioselectivity in ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents

Supplementary files

Article information

Article type
Paper
Submitted
19 Oct 2013
Accepted
30 Nov 2013
First published
18 Nov 2015

Org. Biomol. Chem., 2016,14, 729-737

Author version available

A ligand-controlled switch of regioselectivity in ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents

J. Cao, X. Huang and L. Wu, Org. Biomol. Chem., 2016, 14, 729 DOI: 10.1039/C3OB42084A

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