title: Palladium-catalyzed C-CN activation for intramolecular cyanoesterification of alkynes.
abstract: Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.
authors.affiliation: Department of Chemistry, 207 Pleasant Street, SE, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Naveen R
authors.initials: NR
authors.lastname: Rondla
authors.forename: Samuel M
authors.initials: SM
authors.lastname: Levi
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Ryss
authors.forename: Rachel A
authors.initials: RA
authors.lastname: Vanden Berg
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Douglas