Sulfonyl transfer mechanism in C-S coupling of phenylmagnesium bromide with phenyl arenesulfonates

EROĞLU F., KAHYA N. D., Erdik E.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, cilt.695, sa.2, ss.267-270, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 695 Sayı: 2
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1016/j.jorganchem.2009.09.044
  • Dergi Adı: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.267-270
  • Anahtar Kelimeler: C-S coupling, Grignard reagents, Aryl arenesulfonates, Hammett plot, NUCLEOPHILIC-SUBSTITUTION REACTIONS, ARYL GRIGNARD-REAGENTS, BENZENESULFONATES, CATALYSTS, AMINATION
  • Ankara Üniversitesi Adresli: Evet

Özet

The kinetics of C-S coupling of phenylmagnesium bromide with phenyl arenesulfonates has been studied in THF:toluene (7:10) at 90 degrees C. Kinetic data and Hammett relationship are consistent with an asynchronous S(N)a mechanism in which rate determining thiophilic attack of carbanion takes place much ahead of phenoxy group departure. (C) 2009 Elsevier B.V. All rights reserved.