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Paper | Special issue | Vol 88, No. 2, 2014, pp.1465-1476
Published online, 20th November, 2013
DOI: 10.3987/COM-13-S(S)113
Advances in Siloxane-Based Coupling Reactions: Novel 16-Electron Palladium(0) Tri-alkene Catalysts for Allyl-Aryl Coupling in Precursors to Amaryllidaceae Alkaloids

Frederick E. Nytko, III, Krupa H. Shukla, and Philip DeShong*

*Department of Chemistry and Biochemistry, University of Maryland, 7950 Baltimore Avenue, College Park, MD 20742, U.S.A.


A new class of 16-electron Pd(0) catalysts are surveyed for applications in siloxane based allyl-aryl coupling protocols. The ability to "tune" the catalysts' activity by varying either the cone angle or the electronic characteristics of the alkene ligands attached to palladium was demonstrated. Attempts to prepare chiral adducts in the coupling reaction utilizing chiral bicyclooctadiene derivatives as a ligand for palladium provided no significant enantioenrichment in the coupled product.