Decarbonylative cross-coupling of cyclic anhydrides: introducing stereochemistry at an sp3 carbon in the cross-coupling event.
Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metalacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp3(electrophile)-sp2(nucleophile) cross-coupling and allows for control of stereochemistry during the bond-forming event.
O'Brien
Erin M
EM
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Bercot
Eric A
EA
Rovis
Tomislav
T