Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 43, Pages 13885-13892Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201201301
Keywords
hydrogenation; imines; ketones; metal amidoboranes; reduction
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Funding
- CAS Hundred Talents Project [KGCX2-YW-806]
- Knowledge Innovation Program of CAS [KJCX2-YW-H21]
- National University of Singapore
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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.
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