Issue 18, 2023

Photocatalytic C(sp2)–OMe bond cleavage and amidation of anisoles with N-hydroxyphthalimides and phthalimides

Abstract

The cleavage of the inert C(sp2)–OMe bond via photocatalysis is an attractive alternative to the well-established Ni-catalyzed methods, and is also a challenge in organic chemistry. Herein we report a metal-free photocatalytic C(sp2)–OMe bond cleavage strategy using 4CzIPN as a mild oxidizing photoredox catalyst. N-Hydroxyphthalimides and phthalimides are effective coupling reagents for this C–O bond cleavage and amidation of anisoles, as evidenced by 48 examples. PhthN radical and arene radical cation pathways are suggested for the amidation of anisoles with N-hydroxyphthalimides and phthalimides, respectively.

Graphical abstract: Photocatalytic C(sp2)–OMe bond cleavage and amidation of anisoles with N-hydroxyphthalimides and phthalimides

Supplementary files

Article information

Article type
Research Article
Submitted
08 jun 2023
Accepted
23 jul 2023
First published
25 jul 2023

Org. Chem. Front., 2023,10, 4522-4528

Photocatalytic C(sp2)–OMe bond cleavage and amidation of anisoles with N-hydroxyphthalimides and phthalimides

Z. Pan, M. Wu, J. Fang, A. Zhong, H. Jiang, G. Wang, J. Guo and Y. Ma, Org. Chem. Front., 2023, 10, 4522 DOI: 10.1039/D3QO00861D

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