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Metal Amidoboranes: Superior Double‐Hydrogen‐Transfer Agents in the Reduction of Ketones and Imines
Author(s) -
Xu Weiliang,
Wu Guotao,
Yao Wei,
Fan Hongjun,
Wu Jishan,
Chen Ping
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201301
Subject(s) - chemistry , lithium (medication) , double bond , hydrogen , metal , reduction (mathematics) , transfer hydrogenation , lithium metal , medicinal chemistry , photochemistry , organic chemistry , catalysis , electrode , electrolyte , medicine , geometry , mathematics , ruthenium , endocrinology
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.