Premium
Substrate‐Directed Hydroacylation: Rhodium‐Catalyzed Coupling of Vinylphenols and Nonchelating Aldehydes
Author(s) -
Murphy Stephen K.,
Bruch Achim,
Dong Vy M.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201309987
Subject(s) - hydroacylation , decarbonylation , aryl , chemistry , alkene , regioselectivity , aldehyde , rhodium , reactivity (psychology) , catalysis , organic chemistry , ligand (biochemistry) , alkyl , coupling reaction , combinatorial chemistry , medicine , biochemistry , alternative medicine , receptor , pathology
We report a protocol for the hydroacylation of vinylphenols with aryl, alkenyl, and alkyl aldehydes to form branched products with high selectivity. This cross‐coupling yields α‐aryl ketones that can be cyclized to benzofurans, and it enables access to eupomatenoid natural products in four steps or less from eugenol. Excellent reactivity and high levels of regioselectivity for the formation of the branched products were observed. We propose that aldehyde decarbonylation is avoided by the use of an anionic directing group on the alkene and a diphosphine ligand with a small bite angle.