A brief survey on the copper-catalyzed allylation of alkylzinc and Grignard reagents under Barbier conditions

Erdik E., Kocoglu M.

Applied Organometallic Chemistry, cilt.20, sa.4, ss.290-294, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 20 Sayı: 4
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1002/aoc.1052
  • Dergi Adı: Applied Organometallic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.290-294
  • Anahtar Kelimeler: alkyl Grignard reagents, alkylzinc reagents, allylic coupling, Barbier-Grignard coupling, SUBSTITUTION-REACTION, ENANTIOSELECTIVE SYNTHESIS, ALLYLIC SUBSTITUTION, COUPLING REACTIONS, ORGANOCOPPER, DERIVATIVES, ALKYLATION, INDUCTION, COMPLEXES, ALCOHOLS
  • Ankara Üniversitesi Adresli: Evet

Özet

The same regioselectivity can be obtained in the CuI catalyzed allylic coupling of n-butylzinc reagents prepared by either pre-transmetallation or in situ transmetallation of Grignard reagents in the presence of allylic partner and catalyst. n-Butylzinc bromide and di-n-butylzinc undergo γ-selective allylation whereas tri-n-butylzincate gives preferential α-selectivity. The regioselectivity obtained in the reaction of n-butyl bromide and E-crotyl chloride in the presence of Mg and CuCN is parallel to the coupling of preformed n-butylmagnesium bromide. It is remarkable that the regiochemical outcome of copper catalyzed alkyl-allyl coupling can be controlled by using Grignard reagents prepared under Barbier conditions and alkylzincs prepared by in situ transmetallation. Copyright © 2006 John Wiley & Sons, Ltd.