52374-23-9Relevant academic research and scientific papers
Photoredox-mediated mono- And difluorination of remote unactivated methylene C(sp3)-H bonds of N-alkyl sulfonamides
Deng, Zhiqiang,Zhao, Zhenxiang,He, Gang,Chen, Gong
, p. 3631 - 3635 (2021)
A photoredox-mediated δ-C(sp3)-H fluorination of sulfonyl-protected primary alkylamines with Selectfluor is developed. The reaction can proceed in excellent monofluorination selectivity for amine substrates without α substituent. For α-substituted substrates, a slightly modified reaction conditions with two rounds of operation gives the δ,δ-difluorination products in good yield. Mechanistic studies suggest SET oxidation of sulfonamide group directly generates the key sulfonamide N radical intermediate, which triggers a 1,5-HAT process to form the δ alkyl radical.
Copper-Catalyzed Amide Radical-Directed Cyanation of Unactivated Csp3-H Bonds
Zhang, Hongwei,Zhou, Yulu,Tian, Peiyuan,Jiang, Cuiyu
supporting information, (2019/03/19)
A method for site-selective intermolecular δ/?-Csp3-H cyanation of aliphatic sulfonamides is developed using TsCN as the cyanating reagent, catalyzed by a Cu(I)/phenanthroline complex. The mild, expeditious, and modular protocol allows efficient remote Csp3-H cyanation with good functional group tolerance and high regioselectivity. Mechanistic studies indicate that the reaction might proceed through a Cu(I)-mediated N-F bond cleavage to generate an amidyl radical, 1,5-HAT, and cyano group transfer of the resulting carbon radical with TsCN.
Sulfonamide-Directed Chemo- and Site-Selective Oxidative Halogenation/Amination Using Halogenating Reagents Generated in Situ from Cyclic Diacyl Peroxides
Chang, Denghu,Zhao, Rong,Wei, Congyin,Yao, Yuan,Liu, Yang,Shi, Lei
, p. 3305 - 3315 (2018/03/25)
The combination of cyclic diacyl peroxides with commercially available halide salts as a unique halogenating system is utilized in Hofmann-L?ffler-Freytag-type reaction. This strategy allows for the formation of N-chloroamides, δ-brominated products, and
