Iron/photoredox dual catalysis for acyl nitrene-based C–O bond formation towards phthalides. Issue 98 (21st November 2022)

• Record Type: Journal Article
• Authors: Zhang, Zhide; Deng, Yangling; Hou, Ming; Lai, Xiaojing; Guan, Meng; Zhang, Fengzhi; Qi, Rui; Qiu, Guanyinsheng
• Is Part Of: Chemical communications. Volume 58:Issue 98(2022)
• Page Start: 13644
• Page End: 13647
• Publication Date: 2022-11-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc04917a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : In this work, iron/photoredox dual-catalyzed acyl nitrene formation and the use of acyl nitrene in constructing various C–O bonds are reported for the synthesis of phthalides. 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 SN 1. 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.