Kinetics and mechanism of the C-S coupling reactions of aryl Grignard reagents with aryl arenesulfonates
CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, vol.6, no.2, pp.237-244, 2008 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 6 Issue: 2
- Publication Date: 2008
- Doi Number: 10.2478/s11532-008-0017-4
- Journal Name: CENTRAL EUROPEAN JOURNAL OF CHEMISTRY
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.237-244
- Keywords: Grignard reagents, aryl carbanions, C-S coupling, Hammett plot, activation parameters, BENZENESULFONATES, CATALYSTS, AMINATION, SULFONYL, THF
- Ankara University Affiliated: Yes
Abstract
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.