title: B(C6F5)3-Catalyzed transfer 1,4-hydrostannylation of α,β-unsaturated carbonyls using iPr-tricarbastannatrane.
abstract: Tris(pentafluorophenyl)borane, B(C6F5)3, has been found to be an effective catalyst to access the hydridoborate anion, [N(CH2CH2CH2)3Sn][HB(C6F5)3], via hydride abstraction from the hypercoordinated tin reagent, iPr-tricarbastannatrane. This process has been applied to the B(C6F5)3-catalyzed transfer 1,4-hydrostannylation of electron-deficient olefins, namely benzylidene barbituric acids. Insights into the mechanism have been obtained via a series of1H,2H,11B,13C, and119Sn NMR spectroscopy, mass spectrometry, and labeling experiments.
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, ON N2L 3G1, Canada. efillion@uwaterloo.ca.
authors.forename: Eric
authors.initials: E
authors.lastname: Fillion
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, ON N2L 3G1, Canada. efillion@uwaterloo.ca.
authors.forename: Azadeh
authors.initials: A
authors.lastname: Kavoosi
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, ON N2L 3G1, Canada. efillion@uwaterloo.ca.
authors.forename: Kevin
authors.initials: K
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, ON N2L 3G1, Canada. efillion@uwaterloo.ca.
authors.forename: Christian
authors.identifier: http://orcid.org/0000-0003-4748-6346
authors.initials: C
authors.lastname: Ieritano