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J Org Chem. 1999 Mar 05;64(5):1684-1688. doi: 10.1021/jo982463h.

Cross-Coupling Reactions of Hypervalent Siloxane Derivatives: An Alternative to Stille and Suzuki Couplings.

The Journal of organic chemistry

Molly E. Mowery, Philip DeShong

Affiliations

  1. Department of Chemistry and Biochemistry, The University of Maryland, College Park, Maryland 20742.

PMID: 11674236 DOI: 10.1021/jo982463h

Abstract

Palladium-catalyzed cross-coupling of phenyl, vinyl, and allyl siloxane derivatives proceeded in good to excellent yield with aryl iodides, electron-deficient aryl bromides, and allylic benzoates. Methyl and 2,2,2-trifluoroethyl siloxane derivatives can be employed in the coupling reaction. Electron-donating and -withdrawing groups are tolerated on the aryl halide without affecting the coupling. The scope and limitations of this alternative to Stille and Suzuki couplings is outlined.

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