Abstract
A three-component reaction of alkynes, arylzinc chlorides, and iodomethanes was found to proceed in the presence of a rhodium catalyst to give high yields of trisubstituted/tetrasubstituted alkenes. The usual arylzinc chlorides only gave trisubstituted alkenes, generated through a migratory carbozincation-cross-coupling sequence, where 1,4-Rh migration from an alkenyl carbon to an aryl carbon occurred. In contrast, 5-membered heteroarylzinc chlorides only gave the tetrasubstituted alkenes via a carborhodation-cross-coupling pathway without 1,4-migration.
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