<i>trans</i>-Hydroalkynylation of Internal 1,3-Enynes Enabled by Cooperative Catalysis
Ziyong Wang, Chen Zhang, Jason Wu, Bo Li, Anna Chrostowska, Panaghiotis Karamanis, Shih‐Yuan Liu
Abstract
A cooperative catalyst system involving a Pd(0)/Senphos complex, tris(pentafluorophenyl)borane, copper bromide, and an amine base, is demonstrated to catalyze trans -hydroalkynylation of internal 1,3-enynes. For the first time, a Lewis acid catalyst is shown to promote the reaction involving the emerging outer-sphere oxidative reaction step. The resulting cross-conjugated dieneynes are versatile synthons for organic synthesis, and their characterization reveals distinct photophysical properties depending on the positioning of the donor/acceptor substituents along the conjugation path.
Topics & Concepts
ChemistrySynthonCatalysisBoraneBromideAmine gas treatingConjugated systemLewis acids and basesAcceptorTrisLewis acid catalysisCombinatorial chemistryPolymer chemistryOrganic chemistryPhotochemistryCondensed matter physicsPolymerBiochemistryPhysicsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCatalytic Alkyne Reactions