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- Title
An Insight into Nitromethane as an Organic Nitrile Alternative Source towards the Synthesis of Aryl Nitriles.
- Authors
Saikia, Rakhee; Dey Baruah, Satyajit; Deka, Ramesh C.; Thakur, Ashim J.; Bora, Utpal
- Abstract
Directed by an unusual in situ reduction of CuII, our protocol is a simple CuI‐mediated synthesis of aryl nitriles, with inexpensive and readily available nitromethane as the cyanating source, in moderate to good yields. Exhibiting a wide substrate scope, the method involves simple reaction conditions, is additive free with low catalyst loading. The plausible mechanism of cyanation of aryl halides is elucidated by a congregation of three cycles, namely the in situ reduction of CuII species by nitromethane, generation of HCN species from nitromethane and a regular organometallic pathway which releases the nitrile derivative. The detail of the mechanism of generation of CN– from nitromethane is computationally validated. Our protocol holds the distinction of involving a rarely encountered CuI catalytic species as well as facile in situ generation of nucleophilic CN– to yield synthetically useful aromatic nitriles.
- Subjects
NITROMETHANE; NITRILES; NITRILE derivatives; ARYL halides; CYANIDES
- Publication
European Journal of Organic Chemistry, 2019, Vol 2019, Issue 36, p6211
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201900909