title: Metal amidoboranes: superior double-hydrogen-transfer agents in the reduction of ketones and imines.
abstract: Metal amidoboranes (MABs), such as lithium amidoborane (LiAB), show superior ability in reducing ketones and imines directly into their corresponding secondary alcohols and amines, respectively, at room temperature with high conversion and yields. A mechanistic study indicates that the reduction proceeds through a double-hydrogen-transfer process. Both protic H(N) and hydridic H(B) protons in the amidoborane participate in the reaction. Theoretical investigations show that the first (and rate-determining) step of the reduction reaction is the elimination of LiH from LiAB, followed by the transfer of H(Li) to the C site of the unsaturated bond.
authors.affiliation: Department of Chemistry, National University of Singapore, Singapore.
authors.forename: Weiliang
authors.initials: W
authors.lastname: Xu
authors.forename: Guotao
authors.initials: G
authors.lastname: Wu
authors.forename: Wei
authors.initials: W
authors.lastname: Yao
authors.forename: Hongjun
authors.initials: H
authors.lastname: Fan
authors.forename: Jishan
authors.initials: J
authors.lastname: Wu
authors.forename: Ping
authors.initials: P
authors.lastname: Chen
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D008956:Models, Chemical; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013816:Thermodynamics
chemical_list: D000438:Alcohols; D000588:Amines; D001880:Boranes; D007097:Imines; D007659:Ketones; D018020:Lithium Compounds; D008670:Metals; C571211:lithium amidoborane; D006859:Hydrogen