Controlled reduction of carboxamides to alcohols or amines by zinc hydrides

Controlled reduction of carboxamides to alcohols or amines by zinc hydrides

New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2 ). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives ami...

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Bibliographic Details
Main Authors: Ong, Derek Yiren, Yen, Zhihao, Yoshii, Asami, Imbernon, Julia Revillo, Takita, Ryo, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Alcohols
Amides
Online Access:https://hdl.handle.net/10356/144604
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Institution: Nanyang Technological University
Language: English
Description
Summary:New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2 ). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2 )∞ 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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