Fe-Catalyzed three-component carboazidation of alkenes with alkanes and trimethylsilyl azide. Issue 78 (14th September 2018)

• Record Type: Journal Article
• Authors: Li, Wei-Yu; Wu, Chuan-Shuo; Wang, Zhou; Luo, Yang
• Is Part Of: Chemical communications. Volume 54:Issue 78(2018)
• Page Start: 11013
• Page End: 11016
• Publication Date: 2018-09-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc05090b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Iron out the difference. Carboazidation of alkenes using cycloalkanes, CH2 Cl2, CHCl3 and CCl4 as alkylating reagents proceeded smoothly in the presence of TMSN3, DTBP and a catalytic amount of Fe(acac)3 to afford chain extended alkyl azides and γ-azido chloroalkanes in good to high yields. Abstract : Reported herein is a novel iron-catalyzed, DTBP-mediated carboazidation of alkenes using cycloalkanes, CH2 Cl2, CHCl3 and CCl4 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.