title: Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids.
abstract: A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts.
authors.affiliation: iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China).
authors.forename: Ming-Chen
authors.initials: MC
authors.lastname: Fu
authors.affiliation: iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China). faint123@mail.ustc.edu.cn.
authors.forename: Rui
authors.initials: R
authors.lastname: Shang
authors.affiliation: iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China).
authors.forename: Wan-Min
authors.initials: WM
authors.lastname: Cheng
authors.affiliation: iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei 230026 (China). fuyao@ustc.edu.cn.
authors.forename: Yao
authors.initials: Y
authors.lastname: Fu
mesh_terms: D000478:Alkylation; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure
chemical_list: D000588:Amines; D002264:Carboxylic Acids; D001895:Boron
keywords: alkylation; amines; boron; frustrated Lewis pair; synthetic methods