Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/85737
Title: Reduction of N , N -dimethylcarboxamides to aldehydes by sodium hydride-iodide composite
Authors: Chan, Guo Hao
Ong, Derek Yiren
Yen, Zhihao
Chiba, Shunsuke
Keywords: Amides
Aldehydes
DRNTU::Science::Chemistry
Issue Date: 2018
Source: Chan, G. H., Ong, D. Y., Yen, Z., & Chiba, S. (2018). Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride-Iodide Composite. Helvetica Chimica Acta, 101(5), e1800049-. doi:10.1002/hlca.201800049
Series/Report no.: Helvetica Chimica Acta
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.
URI: https://hdl.handle.net/10356/85737
http://hdl.handle.net/10220/48234
ISSN: 0018-019X
DOI: 10.1002/hlca.201800049
Rights: © 2018 Wiley-VHCA AG, Zurich, Switzerland. All rights reserved. This paper was published in Helvetica Chimica Acta and is made available with permission of Wiley-VHCA AG, Zurich, Switzerland.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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