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: denmarkscs.uiuc.edu
S. E. Denmark, C. R. Butler, J. Am. Chem. Soc., 2008, 130, 3690-3704.
DOI: 10.1021/ja7100888 (free Supporting Information)
see article for more reactions
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.
see article for more examples
formation of silanolate