Synthesis of highly substituted 1,3-dienes through halonium promoted 1,2-sulfur migration of propargylic thioethers

Abstract

Conjugated 1-bromo or 1-iodo-1,3-dienes bearing a sulfide substituent have been synthesized via 1,2-sulfur migration from propargylic thioethers upon activation with NIS or NBS. The reaction generally proceeds with high control over the regio- and diastereoselectivity. Highly substituted thiophenes and selenophenes are easily obtained from the generated dienes.