title: Palladium-catalyzed β-C(sp(3))-H arylation of phthaloyl alanine with hindered aryl iodides: synthesis of complex β-aryl α-amino acids.
abstract: An efficient protocol for palladium-catalyzed β-C(sp(3))-H arylation of aliphatic carboxamides equipped with a 2-(2-pyridyl) ethylamine (PE) auxiliary was developed. The PE auxiliary is uniquely effective at facilitating the arylation of primary C(sp(3))-H bonds with sterically hindered aryl iodides. A variety of aryl iodides bearing alkoxyl, carbonyl, nitro and halogen groups on the ortho position can react with the PE-coupled phthaloyl alanine substrate in moderate to excellent yield. These reactions offer a useful solution for preparing complex β-aryl α-amino acid products from readily accessible starting materials.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China. hegang@nankai.edu.cn gongchen@nankai.edu.cn.
authors.forename: Xuekai
authors.initials: X
authors.lastname: Zhang
authors.forename: Gang
authors.initials: G
authors.lastname: He
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D000409:Alanine / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D007455:Iodine / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D010165:Palladium; D007455:Iodine; D001554:Benzene; D000409:Alanine