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Vinylation of Aromatic Halides Using Inexpensive Organosilicon Reagents. Illustration of Design of Experiment Protocols

Scott E. Denmark* and Christopher R. Butler

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, Email:

S. E. Denmark, C. R. Butler, J. Am. Chem. Soc., 2008, 130, 3690-3704.

DOI: 10.1021/ja7100888

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A variety of aromatic iodides and bromides undergo cross-coupling with divinyltetramethyldisiloxane (DVDS) to give styrenes in good yields in the presence of potassium trimethylsilanoate and catalytic amounts of Pd(dba)2. Triphenylphosphine oxide is needed to extend catalyst lifetime.

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formation of silanolate

Key Words

Styrenes, Hiyama-Denmark Coupling

ID: J48-Y2008-0750