ACS Catalysis
ACS Catalysis
5 years ago

Synergistic Copper/Palladium Catalysis for the Regio- and Stereoselective Synthesis of Borylated Skipped Dienes

Synergistic Copper/Palladium Catalysis for the Regio- and Stereoselective Synthesis of Borylated Skipped Dienes
Jaime Mateos, Eva Rivera-Chao, Martín Fañanás-Mastral
A Cu/Pd-catalyzed allylboration of alkynes with allyl carbonates and bis(pinacolato)diboron to afford borylated skipped dienes is reported. Synergistic Cu and Pd catalysis enables this protocol to work for a wide array of alkynes and allyl carbonates under mild conditions with total regio- and stereocontrol. This transformation features the catalytic generation of β-borylalkenylcopper intermediates and their use in Pd-catalyzed allylic substitution of allyl carbonates. The utility of this method is highlighted by the synthesis of (Z,E)-α-homofarnesene (pheromone) and the terpenoid precursor of Merochlorins (potent antibiotic agents).

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b01833

DOI: 10.1021/acscatal.7b01833

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