Synthesis of P,N-2,2'-biphenyl derivatives with central chirality

• 作 者: JEAN Ludovic POULIQUEN Michael BLANCHET Jérme LASNE Marie-Claire ROUDEN Jacques
• 机 构: Laboratoire de Chimie Moléculaire et Thioorganique,UMR 6507 CNRS-ENSICAEN & Université de Caen-Basse
• 出 处: Science China(Chemistry)
• 发表日期: 2010年09期
• 关键词: biphenyl pyrrolidine chiral equiv aromatic substituted backbone propyl catalyzed

Enantiopure 2-(dicyclohexylphosphino)-1,1’-biphenyl derivatives substituted in the 2’-position by a chiral amino group were prepared.For the compound bearing an acyclic chiral chain,the key step was a Suzuki coupling between bromobenzeneboronic acid and N-Boc-iodoaniline whereas an aromatic nucleophilic substitution allowed the introduction of a chiral pyrrolidine in the 2’-position of the biphenyl backbone.The efficiency of the P,N-biphenyl pyrrolidine derivatives as ligands in Pd-catalyzed arylaminations compares well with that of DavePhos ligand.

Enantiopure 2- (dicyclohexylphosphino) -1,1’-biphenyl derivatives substituted in the 2’-position by a chiral amino group were prepared. For the compound bearing an acyclic chiral chain, the key step was a Suzuki coupling between bromobenzeneboronic acid and N -Boc-iodoaniline, an aromatic nucleophilic substitution allowed the introduction of a chiral pyrrolidine in the 2’-position of the biphenyl backbone. The efficiency of the P, N-biphenyl pyrrolidine derivatives as ligands in Pd-catalyzed arylaminations comparable well with that of DavePhos ligand.