Switching Selectivity in Borylative Allyl–Allyl Cross-Coupling through Synergistic Catalysis
A Cu/Pd-catalyzed borylative coupling of allenes with allyl carbonates is reported. Synergistic Cu/Pd catalysis enables a divergent selectivity compared to Cu catalysis and allows for the regio-, diastereo-, and enantioselective formation of synthetically versatile chiral borylated 1,5-dienes featuring two adjacent tertiary stereocenters. DFT calculations support a closed inner-sphere SE2′ transmetalation between the catalytic allyl copper and allyl palladium intermediates and point at the reductive elimination of the resulting bis(allyl)Pd intermediate as the regio- and diastereo-determining step.
Vázquez-Galiñanes, N.; Sciortino, G.; Piñeiro-Suárez, M.; Tóth, B. L.; Maseras, F.; Fañanás-Mastral, M.
J. Am. Chem. Soc. 2024, 146, 21977-21988
DOI:
10.1021/jacs.4c07188
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