Synthesis and applications of 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl phenylmagnesium chlorides

Abstract

Selective I/Mg exchange reactions of 1,4-diiodo-1,3-dienes and o-iodo-2-(2-iodovinyl)benzenes were achieved viaⁱPrMgCl·LiCl. Various 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl phenylmagnesium chlorides were thus efficiently generated and synthetically applied to afford new C–C bonds via reactions of the alkenyl or aryl C–MgCl bonds with different electrophiles. Useful conjugated compounds including polysubstituted benzenes, naphthalenes and phosphine compounds could be synthesized readily via further applications of the remaining alkenyl C–I bonds and subsequent cyclization reactions.