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 amin...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2019-04, Vol.131 (15), p.5046-5051
Main Authors: Ong, Derek Yiren, Yen, Zhihao, Yoshii, Asami, Revillo Imbernon, Julia, Takita, Ryo, Chiba, Shunsuke
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Alkohole
Amide
Amine
Amines
Chemistry
Halides
Reduction
Reduktionen
Selectivity
Sodium
Sodium hydrides
Zinc
Zinc chloride
Zink
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
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. Mischen und kombinieren: Neue Protokolle zur kontrollierten Reduktion von Carboxamiden zu Alkoholen oder Aminen wurden mit einer Kombination aus Natriumhydrid (NaH) und Zinkhalogeniden (ZnX2) erstellt. Die Art des Halogenids in ZnX2 bestimmt die Selektivität: Das NaH‐ZnI2‐System liefert Alkohole, das NaH‐ZnCl2‐System Amine.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201900233