title: A direct synthesis of allenes by a traceless Petasis reaction.
abstract: A one-pot synthesis of allenes by the 2-nitrobenzenesulfonylhydrazide-mediated coupling of hydroxyaldehydes or ketones with alkynyl trifluoroborate salts is reported. This mild process involves in situ formation of a sulfonylhydrazone that reacts with alkynyl trifluoroborates to generate a transient propargylic hydrazide species. Decomposition of this unstable hydrazide via an intermediate monoalkyldiazine produces the allene products through an alkene walk mechanism.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
authors.forename: Devon A
authors.initials: DA
authors.lastname: Mundal
authors.forename: Kelly E
authors.initials: KE
authors.lastname: Lutz
authors.forename: Regan J
authors.initials: RJ
authors.lastname: Thomson