Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C-N and C-O coupling reactions

作者：Majumder Arpi; Gupta Ragini^*; Mandal Mrinmay; Babu Madhu; Chakraborty Debashis

来源：Journal of Organometallic Chemistry, 2015, 781: 23-34.

DOI：10.1016/j.jorganchem.2014.11.018

• Ullmann-type reaction
• Cross-coupling
• Air-stable Pd(0)-catalyst
• C-N bond formation
• C-O bond formation

This paper describes an efficient procedure for palladium(0)-catalyzed N-arylation and O-arylation of aryl halides by Ullmann-type cross coupling reaction under mild reaction conditions in a short reaction time. Two phosphine sulphide ligands and their corresponding Pd(0) complexes namely [Pd(p(2)S(2))(dba)] and [Pd(pp(3)S(4))(dba)], were synthesized, where p(2)S(2) is 1,2-bis(diphenylphosphino) ethane disulfide, pp(3)S(4) is tris[2-(diphenylphosphino) ethyl] phosphine tetrasulfide and dba is dibenzylideneacetone. Optimal reaction conditions were determined for the arylation reactions using iodobenzene and benzimidazole by varying temperature, solvent, base and catalyst loading. The cross coupling reactions were carried out taking iodobenzenes/bromobenzenes and a wide variety of substituted aryl amines/phenols/alcohols with different steric and electronic properties to afford the desired N-aryl amines/diaryl ethers/alkyl aryl ethers in good to excellent yield (70e94%).

• 出版日期2015-4-1