Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite

Guo Hao Chan, Derek Yiren Ong, Zhihao Yen, Shunsuke Chiba

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

A new and concise protocol for selective reduction of N,N-dimethylamides into aldehydes was established using sodium hydride (NaH) in the presence of sodium iodide (NaI) under mild reaction conditions. The present protocol with the NaH-NaI composite allows for reduction of not only aromatic and heteroaromatic but also aliphatic N,N-dimethylamides with wide substituent compatibility. Retention of α-chirality in the reduction of α-enantioriched amides was accomplished. Use of sodium deuteride (NaD) offers a new step-economical alternative to prepare deuterated aldehydes with high deuterium incorporation rate. The NaH-NaI composite exhibits unique chemoselectivity for reduction of N,N-dimethylamides over ketones.

Original languageEnglish
Article numbere1800049
JournalHelvetica Chimica Acta
Volume101
Issue number5
DOIs
Publication statusPublished - May 2018
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VHCA AG, Zurich, Switzerland

ASJC Scopus Subject Areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Keywords

  • aldehydes
  • amides
  • iodide
  • reduction
  • sodium hydride

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