Cu‐Catalyzed Polychloromethylamination of Styrenes through C(sp³)−H Bond Cleavage

Abstract

A copper-catalyzed three-component coupling reaction has been developed allowing the rapid building of valuable complex highly functionalized β-polychloromethyl amines from simple styrenes, arylamines, and dichloromethane/chloroform. Using aryldiazonium salts as a radical initiator, a series of corresponding products are obtained with moderate to good yields under a carbon dioxide or nitrogen atmosphere (50 psi). In addition, good functional group tolerance can be observed.

Iron-catalyzed carboamination of vinylarenes with alkanes and nitrogen nucleophiles

“…9 We also realized the 1,2-carboamination of alkenes with arylamines and dichloromethane/chloroform using aryldiazonium salts as a radical initiator (Scheme 1C). 10 In view of these limitations and our continuous interest in 1,2-carboamination of alkenes, we realized the 1,2-carboamination of alkenes with unactivated alkanes and weakly nucleophilic amides/sulfonamides (Scheme 1D).…”

“…9 We also realized the 1,2-carboamination of alkenes with arylamines and dichloromethane/chloroform using aryldiazonium salts as a radical initiator (Scheme 1C). 10…”

Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage

“…Against this background and based on our continual interest in the difunctionalization of alkenes, [9] we wish to report here our new processes for the Co-catalyzed three-component carboamination/carboarylation of alkenes by CH 3 CN and aromatic anilines/indoles (Scheme 1, 3). The reaction is characterized by simple and important substrates, furnishing valuable complex highly functionalized scaffolds that are otherwise difficult to access.…”