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Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H‐Abstraction by Azide Radical
Author(s) -
Shee Maniklal,
Shah Sk. Sheriff,
Singh N. D. Pradeep
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001332
Subject(s) - chemistry , aryl , photocatalysis , azide , organic chemistry , photochemistry , catalysis , alkyl
This report presents the visible‐light‐assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O 2 . Organic photoredox catalyst, 4CzIPN (1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene), induces single electron transfer (SET) from azide N 3 − and generates azide radical N 3 ⋅.The photogenerated N 3 ⋅ abstracts H atom from α‐C−H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN 3 ) 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.