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; Kalman J Szabó

doi:10.1021/ja062585o

Palladium-catalyzed coupling of allylboronic acids with iodobenzenes. Selective formation of the branched allylic product in the absence of directing groups

J Am Chem Soc. 2006 Jun 28;128(25):8150-1. doi: 10.1021/ja062585o.

Authors

Sara Sebelius¹, Vilhelm J Olsson, Olov A Wallner, Kalman J Szabó

Affiliation

¹ Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.

PMID: 16787075
DOI: 10.1021/ja062585o

Abstract

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 (eta3-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.