Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical

Chemistry : a European Journal
Pradeep SinghN D Pradeep Singh

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.

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Citations

Mar 4, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Pengyan LiDongpeng Yan
May 19, 2021·Chemical Society Reviews·Megan Amy Bryden, Eli Zysman-Colman

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