Verkade Base in FLP Chemistry–From Stoichiometric C–H Bond Cleavage to the Catalytic Dimerization of Alkynes
Amandeep Brar, Suresh Mummadi, Daniel K. Unruh, Clemens Krempner
Abstract
Stoichiometric and catalytic reactions of terminal alkynes with various FLPs and Lewis acid–base adducts have been investigated. Reactions of phenylacetylene with FLPs composed of the Verkade base N[CH2CH2NPri]3P (1) and the Lewis acids BPh3, 9-hexyl-BBN, and 9-BBN gave [N(CH2CH2NPri)3PH][PhC≡C-BPh3] (2), [N(CH2CH2NPri)3PH][9-hexyl-9-PhC≡C-BBN] (3), and [N(CH2CH2NPri)3PH][9-PhCH═CH-9-PhC≡C-BBN] (4). The binuclear Lewis acid–base adduct (C6F5)3Al–N[CH2CH2NPri]3P–Al(C6F5)3 (6) effectively catalyzed the dimerization of terminal alkynes to gem-1,3-enynes.
Topics & Concepts
ChemistryPhenylacetyleneAdductLewis acids and basesCatalysisStoichiometryMedicinal chemistryCleavage (geology)Base (topology)StereochemistryOrganic chemistryMathematicsGeotechnical engineeringFracture (geology)EngineeringMathematical analysisOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsLuminescence and Fluorescent Materials