A catalytic process based on sequential ortho-alkylation and vinylation of ortho-alkylaryl iodides via palladacycles

A new synthesis of vinylarenes selectively substituted in both their ortho positions with different alkyl groups is reported The reaction occurs starting from ortho-alkyl substituted iodoarenes which are caused to react with aliphatic iodides, terminal olefins, K2CO3, AcOK and Pd(OAc)(2) in a one-pot reaction consisting of a series of elementary steps controlled by palladium in its oxidation stales 0, II and IV. A correct balance of all the steps involved is required to obtain a catalytic reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.