Fe-Catalyzed three-component carboazidation of alkenes with alkanes and trimethylsilyl azide

Reported herein is a novel iron-catalyzed, DTBP-mediated carboazidation of alkenes using cycloalkanes, CH 2 Cl 2 , CHCl 3 and CCl 4 as alkylating reagents to generate electrophilic or nucleophilic alkyl radicals. Mechanistic studies suggested that the reaction proceeded via the addition of alkyl radicals to alkenes followed by an iron-mediated ligand transfer process. The reaction is unique as it is applicable not only to diversely functionalized electron rich alkenes, but also to electron-poor olefins to provide chain extended azides and γ-azido chloroalkanes in good to high yields. Iron out the difference. Carboazidation of alkenes using cycloalkanes, CH 2 Cl 2 , CHCl 3 and CCl 4 as alkylating reagents proceeded smoothly in the presence of TMSN 3 , DTBP and a catalytic amount of Fe(acac) 3 to afford chain extended alkyl azides and γ-azido chloroalkanes in good to high yields.