Visible Light Mediated Chemoselective Hydroxylation of Benzylic Methylenes

We have developed a metal-free photocatalytic selective hydroxylation of benzylic methylenes to secondary alcohols. This approach utilizes low-cost eosin Y as photocatalyst, O2 as green oxidant, and inexpensive triethylamine as inhibitor for overoxidation. The mild reaction conditions enable the pro...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-02, Vol.89 (4), p.2656-2664
Main Authors: Tan, Zhiyong, Chen, Tingting, Zhu, Jinbin, Luo, Wenjun, Yu, Daohong, Guo, Wei
Format: Article
Language:English
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Summary:We have developed a metal-free photocatalytic selective hydroxylation of benzylic methylenes to secondary alcohols. This approach utilizes low-cost eosin Y as photocatalyst, O2 as green oxidant, and inexpensive triethylamine as inhibitor for overoxidation. The mild reaction conditions enable the production of secondary alcohols with 56–95% yields, making it a promising and environmental-friendly method for the synthesis of secondary alcohols from benzylic methylenes.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02683