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Site‐Selective Remote Radical C−H Functionalization of Unactivated C−H Bonds in Amides Using Sulfone Reagents
Author(s) -
Xia Yong,
Wang Lin,
Studer Armido
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807455
Subject(s) - surface modification , chemistry , sulfone , intramolecular force , moiety , reagent , hydrogen bond , combinatorial chemistry , photochemistry , stereochemistry , polymer chemistry , organic chemistry , molecule
A general and practical strategy for remote site‐selective functionalization of unactivated aliphatic C−H bonds in various amides by radical chemistry is introduced. C−H bond functionalization is achieved by using the readily installed N‐allylsulfonyl moiety as an N‐radical precursor. The in situ generated N‐radical engages in intramolecular 1,5‐hydrogen atom transfer to generate a translocated C radical which is subsequently trapped with various sulfone reagents to afford the corresponding C−H functionalized amides. The generality of the approach is documented by the successful remote C−N 3 , C−Cl, C−Br, C−SCF 3 , C−SPh, and C−C bond formation. Unactivated tertiary and secondary C−H bonds, as well as activated primary C−H bonds, can be readily functionalized by this method.