Palladium catalyzed coupling of organotin reagents with organic electrophiles

Abstract

A novel, synthetically useful palladium catalyzed cross-coupling reaction of organotin reagents with a variety of organic electrophiles that generates a new carbon-carbon bond has been discovered recently. Because this mild, versatile reaction is tolerant of a wide variety of organic functionality on either coupling partner, is stereospecific, and gives high yields, it is ideal for use in the synthesis of complicated organic molecules. In the presence of carbon monoxide, instead of a direct coupling reaction, carbon monoxide insertion takes place, stitching the coupling partners together and generating a ketone. The utility of this coupling reaction has been demonstrated by the synthesis of a macrodiolide antibiotic, marine sesquiterpenes, insect pheremones and a number of key synthetic intermediates. © 1985 IUPAC