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Reduction of N , N ‐Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite
Author(s) -
Chan Guo Hao,
Ong Derek Yiren,
Yen Zhihao,
Chiba Shunsuke
Publication year - 2018
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201800049
Subject(s) - chemistry , iodide , sodium hydride , hydride , sodium iodide , chemoselectivity , deuterium , substituent , sodium , medicinal chemistry , organic chemistry , hydrogen , catalysis , physics , quantum mechanics
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.