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- Title
Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H‐Abstraction by Azide Radical.
- Authors
Shee, Maniklal; Shah, Sk. Sheriff; Singh, N. D. Pradeep
- Abstract
This report presents the visible‐light‐assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene), induces single electron transfer (SET) from azide N3− and generates azide radical N3⋅.The photogenerated N3⋅ abstracts H atom from α‐C−H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Brønsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.
- Subjects
BENZYL alcohol; AROMATIC compounds; NITRILES; HYDRONITRIC acid; METHANOL; BENZENEDICARBONITRILE
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 62, p14070
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202001332