Experimental and theoretical studies on the oxidative addition of palladium(0) to beta-chlorovinamidinium salts

Authors
Davies, IW Wu, J Marcoux, JF Taylor, M Hughes, D Reider, PJ Deeth, RJ
Citation
Iw. Davies et al., Experimental and theoretical studies on the oxidative addition of palladium(0) to beta-chlorovinamidinium salts, TETRAHEDRON, 57(24), 2001, pp. 5061-5066
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
24
Year of publication
2001
Pages
5061 - 5066
Database
ISI
SICI code
0040-4020(20010611)57:24<5061:EATSOT>2.0.ZU;2-9
Abstract
Boronic acids, esters and borinic anhydrides are partners in Suzuki-Miyaura cross-coupling reactions with a variety of beta -chlorovinamidinium salts to give the desired beta -arylvinamidinium salts in up to 88% yield. Reduct ion is a competing reaction pathway. DFT calculations on the intermediate p alladium complex reveal that the Pd-C interaction is predominantly of a-sym metry and the metal based LUMO is mainly d(z2) in character. (C) 2001 Elsev ier Science Ltd. All rights reserved.