Decarbonylative Cross-Coupling of Cyclic Anhydrides: Introducing Stereochemistry at an sp3 Carbon in the Cross-Coupling Event
- 7 August 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (35), 10498-10499
- https://doi.org/10.1021/ja036290b
Abstract
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.Keywords
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