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Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
Author(s) -
Ong Derek Yiren,
Yen Zhihao,
Yoshii Asami,
Revillo Imber Julia,
Takita Ryo,
Chiba Shunsuke
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201900233
Subject(s) - zinc , halide , chemistry , hydride , alcohol , sodium hydride , selectivity , inorganic chemistry , combinatorial chemistry , organic chemistry , catalysis , metal
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX 2 ). Use of a different halide on ZnX 2 dictates the selectivity, wherein the NaH‐ZnI 2 system delivers alcohols and NaH‐ZnCl 2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH 2 ) ∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H−Zn−Cl) 2 is the key species for the production of amines.