Convenient one-pot synthesis of (E)-beta-aryl vinyl halides from benzyl bromides and dihalomethanes.
(E)-beta-aryl vinyl iodides are synthesized in high yield with excellent stereoselectivity from benzyl bromides by a one-pot homologation/stereoselective elimination procedure. Convenient conditions involving the anion of diiodomethane and an excess of base provide complete consumption of the benzyl bromide and elimination from a diiodoalkane intermediate. Similar conditions provide (E)-beta-aryl vinyl chlorides and bromides by employing the anions of ICH(2)Cl or CH(2)Br(2). The functional group tolerance and facile purification allows rapid access to a wide range of functionalized vinyl halides.
Bull
James A
JA
Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7.
Mousseau
James J
JJ
Charette
André B
AB