Kinetics and mechanism of the C-S coupling reactions of aryl Grignard reagents with aryl arenesulfonates

Erdik E., EROĞLU F.

CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, cilt.6, sa.2, ss.237-244, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 6 Sayı: 2
  • Basım Tarihi: 2008
  • Doi Numarası: 10.2478/s11532-008-0017-4
  • Dergi Adı: CENTRAL EUROPEAN JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.237-244
  • Anahtar Kelimeler: Grignard reagents, aryl carbanions, C-S coupling, Hammett plot, activation parameters, BENZENESULFONATES, CATALYSTS, AMINATION, SULFONYL, THF
  • Ankara Üniversitesi Adresli: Evet

Özet

The kinetics of the C-S coupling of arylmagnesium bromides with phenyl tosylate has been studied in THF: toluene at 90 degrees C. The reaction is first order in Grignard reagent and first order in phenyl tosylate. Kinetic data, Hammett relationship and activation parameters are consistent with a nucleophilic addition mechanism involving rate determining attack of carbanion to sulfonyl group followed by a fast phenoxide group leaving.