Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

Derek Yiren Ong; Zhihao Yen; Asami Yoshii; Julia Revillo Imbernon; Ryo Takita; Shunsuke Chiba

doi:10.1002/anie.201900233

Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

Derek Yiren Ong, Zhihao Yen, Asami Yoshii, Julia Revillo Imbernon, Ryo Takita^*, Shunsuke Chiba

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4992-4997
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	15
DOIs	https://doi.org/10.1002/anie.201900233
Publication status	Published - Apr 1 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

alcohols
amides
amines
reduction
zinc

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10.1002/anie.201900233

Cite this

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abstract = " 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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Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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