Issue 98, 2022
From the journal:

Chemical Communications

Iron/photoredox dual catalysis for acyl nitrene-based C–O bond formation towards phthalides†

Zhide Zhang,ab   Yangling Deng,b   Ming Hou,b   Xiaojing Lai,b   Meng Guan,b   Fengzhi Zhang,*ac   Rui Qib  and  Guanyinsheng Qiu ORCID logo b  

* Corresponding authors

a College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang, China

b College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang, China
E-mail: qiuguanyinsheng@mail.zjxu.edu.cn

c School of Pharmaceutical Sciences, Hangzhou Medical College, Hangzhou, Zhejiang, China

Abstract

This paper describes iron/photoredox dual-catalyzed acyl nitrene formation and the use of acyl nitrene in constructing various C–O bonds towards phthalides. The developed reaction starts from N-methoxyl-2-alkylbenzamides. Mechanism surveys suggest the reaction involves iron nitrene-based hydrogen atom abstraction (HAA), radical-polar crossover and O-nucleophilic SN1. Distinctively, the often-reported radical rebound in previous publications is not observed. The reaction represents the first example on acyl nitrene-based synthesis of phthalides. Moreover, it also serves as a supplement for the synthesis of marketed medicines such as 3-butylphthalides (NBP), thalidomide, Pomalyst and Otezia.

Graphical abstract: Iron/photoredox dual catalysis for acyl nitrene-based C–O bond formation towards phthalides

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Article information

DOI
https://doi.org/10.1039/D2CC04917A
Article type
Communication
Submitted
06 Sep 2022
Accepted
14 Nov 2022
First published
14 Nov 2022

Chem. Commun., 2022,58, 13644-13647

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Iron/photoredox dual catalysis for acyl nitrene-based C–O bond formation towards phthalides

Z. Zhang, Y. Deng, M. Hou, X. Lai, M. Guan, F. Zhang, R. Qi and G. Qiu, Chem. Commun., 2022, 58, 13644 DOI: 10.1039/D2CC04917A

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