Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 36, Pages 6211-6216Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900909
Keywords
Aryl nitriles; Copper; Cyanation; Reduction; Nitromethane
Categories
Funding
- Department of Science and Technology, New Delhi [EMR/2016/005944]
- Tezpur University
- Department of Science and Technology, New Delhi
Ask authors/readers for more resources
Directed by an unusual in situ reduction of Cu-II, our protocol is a simple Cu-I-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 Cu-II 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 Cu-I catalytic species as well as facile in situ generation of nucleophilic CN- to yield synthetically useful aromatic nitriles.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available