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 language | English |
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Article number | e1800049 |
Journal | Helvetica Chimica Acta |
Volume | 101 |
Issue number | 5 |
DOIs | |
Publication status | Published - May 2018 |
Externally published | Yes |
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