N -Sulfonylaminophthalimide-Catalyzed Aerobic Oxidative Cleavage of α-C(sp 3 )–H and β,γ-C(sp 3 )–C(sp 3 ) Bonds of Tertiary Amines

Organic Letters 2026

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Authors: Yixia Wang, Zhuoya Chen, Y Wei, Tao Chen, Ze‐Feng Xu, Miao Yu, C R Li
DOI: 10.1021/acs.orglett.6c02649
Cited by: 1
References: 43

Abstract

-sulfonylaminophthalimide (NSAPI)-catalyzed one-stop solution for aerobic oxidization of tertiary amine, including α-C-H carbonylation and β,γ-C-C bond cleavage, under mild conditions was reported, affording the corresponding formamide in moderate to excellent yields. The protocol exhibits broad substrate scope, tolerating a wide range of tertiary anilines, aryl morpholines, and piperazine derivatives with various electronic and steric properties. Mechanistic studies, including radical trapping experiments and HRMS analysis, support a radical-mediated pathway initiated by deprotonation and oxidation of NSAPI, followed by α-C-H hydrogen atom abstraction, peroxyl radical formation, and subsequent C-C bond scission.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Oxidative Organic Chemistry Reactions Radical Photochemical Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
28
Pages
9107–9112
Publication date
6 July 2026
Language
EN