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

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.

Key words

aryl cyclopropylketones - carbon monoxide - carbonylative cross-coupling - NHC ligand - palladium - tricyclopropylbismuth

• References and Notes

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• 52 Method B Same as method A except that 1.5 equiv of tricyclopropylbismuth (2a) instead of 1.0 equiv and 0.1 equiv of (SIPr)Pd(allyl)Cl instead of 0.05 equiv were used, and that the reaction was heated at 80 °C instead of 40 °C.

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