Issue 76, 2017

Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect

Abstract

A Ni-catalyzed ring-opening of α-hydroxycyclobutenones is reported herein. A remarkable ligand effect was observed during transformations following the ring-opening. The employment of PPh3 leads to the formation of 2-furanones 2 through a migration of an alkoxyl group, and 2-furanones 3 were generated through a migration of hydrogen in the presence of Xantphos, affording a divergent approach to 2-furanones bearing multiple functional groups.

Graphical abstract: Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect

Supplementary files

Article information

Article type
Communication
Submitted
29 Apr 2017
Accepted
04 Sep 2017
First published
04 Sep 2017

Chem. Commun., 2017,53, 10540-10543

Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect

S. Gao and X. Hu, Chem. Commun., 2017, 53, 10540 DOI: 10.1039/C7CC03340K

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