Synthetic utility of the palladium-catalyzed coupling reaction of acid chlorides with organotins

JW Labadie, D Tueting, JK Stille

Index: Labadie, Jeff W.; Tueting, David; Stille, J. K. Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4634 - 4642

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Citation Number: 225

Abstract

The palladium coupling of acid chlorides with unsymmetrical organotin reagents R” 3SnR'can be carried out in chloroform under mild conditions in high yields to give the ketone RCOR'in which only one of the four organic groups on tin appears in the ketone product. Alkyl partners (R'= methyl or butyl) on tin serve as anchoring groups and do not transfer. When R'is acetylenic, vinyl, aryl, methoxymethylene, allyl, or benzyl, transmetalation takes ...