Highly efficient synthesis of arylsulfide derivatives from coupling reaction of aryl titanium reagents with N-aryl thiosuccinimides catalyzed by copper under ligand-free conditions

Abstract

A highly efficient and simple cross-coupling reactions of aryltitanium reagents with N-aryl thiosuccinimides for the synthesis of arylsulfide derivatives using Cu(acac)2 (20 mol%) as catalyst are reported. Under the optimum reaction conditions, the coupling reaction between (hetero)aryltitanium reagents with N-aryl thiosuccinimides can be carried out smoothly, 18–93 % isolated yields of arylsulfides were obtained. In addition, 1-(pyridin-2-ylthio)pyrrolidine-2,5-dione and 1-(isobutylthio)pyrrolidine-2,5-dione worked efficiently with aryltitanium reagent as well. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize arylsulfide derivatives. The method avoids the use of expensive transition metals, such as Pd, Ir or Rh, phosphine ligands, and has the advantages of simple operation and high reaction efficiency.2009 Elsevier Ltd. All rights reserved.