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Cross-Coupling of Aromatic Bromides with Allylic Silanolate Salts

Scott E. Denmark* and Nathan S. Werner

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, Email: denmarkscs.uiuc.edu

S. E. Denmark, N. S. Werner, J. Am. Chem. Soc., 2008, 130, 16382-16393.

DOI: 10.1021/ja805951j (free Supporting Information)


Abstract

Sodium allyldimethylsilanolates and 2-butenyldimethylsilanolates undergo cross-coupling with a wide variety of aryl bromides to afford allylated and crotylated arenes. Reactions of  allyldimethylsilanolate take place in DME with allylpalladium chloride dimer whereas 2-butenyldimethylsilanolate delivered branched products in toluene in the presence of Pd(dba)2 and norbornadiene as ligand.

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Key Words

Allylation, Hiyama-Denmark Coupling


ID: J48-Y2008-3630