title: Asymmetric N-H insertion of secondary and primary anilines under the catalysis of palladium and chiral guanidine derivatives.
abstract: Efficient enantioselective NH insertion reactions of secondary and primary anilines were catalyzed by palladium(0) in combination with chiral guanidine derivatives. A broad range of substituted anilines were tolerated, and the corresponding products were obtained in high yield (up to 99 %) with good enantioselectivity (up to 94 % ee) under mild reaction conditions. The NH insertion mechanism was examined by the study of kinetic isotope effects, control experiments, HRMS, and spectroscopic analysis.
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Yin
authors.initials: Y
authors.lastname: Zhu
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Shunxi
authors.initials: S
authors.lastname: Dong
authors.forename: Yuhang
authors.initials: Y
authors.lastname: Zhou
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D019791:Guanidine / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007700:Kinetics; D009584:Nitrogen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000814:Aniline Compounds; D010165:Palladium; D006859:Hydrogen; D019791:Guanidine; D009584:Nitrogen; C023650:aniline
keywords: NH insertion; guanidine derivatives; palladium; secondary amines; α-diazoesters