Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing Groups

Sara Sebelius, Vilhelm J. Olsson, Olov A. Wallner, and Kálmán J. Szabó*
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden
J. Am. Chem. Soc., 2006, 128 (25), pp 8150–8151
DOI: 10.1021/ja062585o
Publication Date (Web): June 7, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kalman@organ.su.se

Abstract

Abstract Image

Palladium-catalyzed coupling reactions of functionalized allylboronic acids with iodobenzenes were achieved under standard Suzuki−Miyaura coupling conditions. The coupling reactions afforded selectively the branched allylic products in high to excellent yields. In contrast to palladium-catalyzed nucleophilic substitution reactions proceeding via (η3-allyl)palladium intermediates, this process does not require directing groups in the allyl moiety to achieve substitution at the congested allylic terminus. The regioselectivity of the process was largely unaffected by the substituent effects of the iodobenzenes and the allylic substrates.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue June 28, 2006
  • Received April 13, 2006

Recommend & Share

Related Content

Other ACS content by these authors: