Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides | Zendy

Ong Derek Yiren | Zendy; Yen Zhihao | Zendy; Yoshii Asami | Zendy; Revillo Imber Julia | Zendy; Takita Ryo | Zendy; Chiba Shunsuke | Zendy

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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.

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