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Decarbonylative cross-coupling of cyclic anhydrides: introducing stereochemistry at an sp3 carbon in the cross-coupling event.

作者信息

O'Brien Erin M, Bercot Eric A, Rovis Tomislav

机构信息

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.

出版信息

J Am Chem Soc. 2003 Sep 3;125(35):10498-9. doi: 10.1021/ja036290b.

DOI:10.1021/ja036290b
PMID:12940714
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.

摘要

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