Structural requirements for palladium catalyst transfer on a carbon-carbon double bond

Masataka Nojima; Yoshihiro Ohta; Tsutomu Yokozawa

doi:10.1021/jacs.5b03113

Structural requirements for palladium catalyst transfer on a carbon-carbon double bond

J Am Chem Soc. 2015 May 6;137(17):5682-5. doi: 10.1021/jacs.5b03113. Epub 2015 Apr 28.

Authors

Masataka Nojima¹, Yoshihiro Ohta¹, Tsutomu Yokozawa¹

Affiliation

¹ Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan.

PMID: 25900778
DOI: 10.1021/jacs.5b03113

Abstract

Intramolecular transfer of (t)Bu3PPd(0) on a carbon-carbon double bond (C═C) was investigated by using Suzuki-Miyaura coupling reaction of dibromostilbenes with aryl boronic acid or boronic acid esters in the presence of various additives containing C═C as a model. Substituent groups at the ortho position of C═C of stilbenes are critical for selective intramolecular catalyst transfer and may serve to suppress formation of the bimolecular C═C-Pd-C═C complex that leads to intermolecular transfer of (t)Bu3PPd(0).