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

Synthesis of P,N-2,2'-biphenyl derivatives with central chirality
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摘要 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 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.
出处 《Science China Chemistry》 SCIE EI CAS 2010年第9期1907-1913,共7页 中国科学(化学英文版)
基金 the Ministry of Education, the CNRS and the European Union (FEDER funding) for financial supports
关键词 3-aminopyrrolidines SUZUKI coupling BIPHENYLS CHIRAL LIGAND arylamination 3-aminopyrrolidines Suzuki coupling biphenyls chiral ligand arylamination
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