title: Rhodium(III)-Catalyzed Activation of C(sp3)-H Bonds and Subsequent Intermolecular Amidation at Room Temperature.
abstract: Disclosed herein is a Rh(III)-catalyzed chelation-assisted activation of unreactive C(sp3)-H bonds, thus enabling an intermolecular amidation to provide a practical and step-economic route to 2-(pyridin-2-yl)ethanamine derivatives. Substrates with other N-donor groups are also compatible with the amidation. This protocol proceeds at room temperature, has a relatively broad functional-group tolerance and high selectivity, and demonstrates the potential of rhodium(III) in the promotive functionalization of unreactive C(sp3)-H bonds. A rhodacycle having a SbF6(-) counterion was identified as a plausible intermediate.
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China).
authors.forename: Xiaolei
authors.initials: X
authors.lastname: Huang
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China).
authors.forename: Yan
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China).
authors.forename: Jingbo
authors.initials: J
authors.lastname: Lan
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China). jsyou@scu.edu.cn.
authors.forename: Jingsong
authors.initials: J
authors.lastname: You
mesh_terms: D000577:Amides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry; D008968:Molecular Conformation; D012238:Rhodium / Q000737:chemistry*; D013696:Temperature
chemical_list: D000577:Amides; D002244:Carbon; D006859:Hydrogen; D012238:Rhodium
keywords: CH activation; X-ray diffraction; heterocycles; rhodium; sulfonamides