title: Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino Acid Esters.
abstract: A novel dehydrogenative cross-coupling (DCC) reaction between N-arylglycine esters and phenols or 1,3,5-trimethoxybenzene was developed by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant. Under optimized conditions, a range of N-arylglycine esters 1 underwent the DCC reaction smoothly with various phenols 2 or 1,3,5-trimethoxybenzene 4 to give desired α-aryl α -amino acid esters 3 or 5, respectively, with high ortho regioselectivities in a moderate to excellent yield. A possible mechanism involving aromatic electrophilic substitution is proposed.
authors.affiliation: Department of Chemistry, Zhejiang University , Hangzhou 310028, P. R. China.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Salman
authors.affiliation: Department of Chemistry, Zhejiang University , Hangzhou 310028, P. R. China.
authors.forename: Zhi-Qiang
authors.initials: ZQ
authors.lastname: Zhu
authors.affiliation: Department of Chemistry, Zhejiang University , Hangzhou 310028, P. R. China.|State Key Laboratory of Elemento-organic Chemistry, Nankai University , Tianjin 300071, P. R. China.
authors.forename: Zhi-Zhen
authors.initials: ZZ
authors.lastname: Huang
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D004952:Esters; D010636:Phenols; C015560:1,3,5-trimethoxybenzene; D010696:Phloroglucinol; D005998:Glycine