Synlett
DOI: 10.1055/s-0036-1590832
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction between Aryl(Heteroaryl) Iodides and Tricyclopropylbismuth: Expedient Access to Aryl Cyclopropylketones

Emeline Benoit, Julien Dansereau, Alexandre Gagnon*
  • Département de Chimie, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada   Email: gagnon.alexandre@uqam.ca
This work was supported by a provincial Fonds de Recherche du Québec, Nature et Technologies (FRQNT) team grant and by the Centre in Green Chemistry and Catalysis (CGCC).
Further Information

Publication History

Received: 24 May 2017

Accepted after revision: 20 June 2017

Publication Date:
19 July 2017 (eFirst)

Dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

The carbonylative cross-coupling reaction between aryl and heteroaryl iodides and tricyclopropylbismuth is reported. The reaction is catalyzed by (SIPr)Pd(allyl)Cl, a NHC-palladium(II) catalyst, operates under 1 atm of carbon monoxide and tolerates a wide range of functional groups. The use of lithium chloride was found to provide higher yields of the desired aryl cyclopropylketones. The conditions were also applied to the carbonylative cross-coupling of an iodoalkene to afford the corresponding alkenyl cyclopropylketone.

Supporting Information