title: Efficient carboazidation of alkenes using a radical desulfonylative azide transfer process.
abstract: The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
authors.forename: Karin
authors.initials: K
authors.lastname: Weidner
authors.forename: André
authors.initials: A
authors.lastname: Giroult
authors.forename: Philippe
authors.initials: P
authors.lastname: Panchaud
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D013441:Sulfinic Acids / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000475:Alkenes; D001386:Azides; D007094:Imides; D007202:Indicators and Reagents; D013441:Sulfinic Acids; C431548:lepadiformine; C038867:diazene