Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
- 17 January 2020
- journal article
- research article
- Published by American Association for the Advancement of Science (AAAS) in Science
- Vol. 367 (6475), 281-285
- https://doi.org/10.1126/science.aay9501
Abstract
The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.Funding Information
- NSFC (21632001, 21772002, 81821004)
- The National Basic Research Program of China (No. 2015CB856600)
- the Drug Innovation Major Project (2018ZX09711-001)
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