Vinylation of Aromatic Substrates with Solvolytically Generated Trisubstituted Vinyl Cations

Article abstract of DOI:10.1021/jo00146a033

Vinylation of aromatic compounds by α-aryl-β,β-disubstituted vinyl bromides (3a-i) in the presence of silver salts and 2,6-lutidine or 2,6-di-tert-butyl-4-methylpyridine proceed with high yields.The silver triflate assisted reaction is preferable to the silver tetrafluoroborate assisted reaction.The reaction of 1-anisyl-2,2-diphenylvinyl bromide gives a ρ⁺ value of -4.08 and high intramolecular selectivity with k_o/k_p ratios of 6.2-78.It is suggested that the reaction proceeds via intermediate α-arylvinyl cations and that the inter- and intramolecular selectivities are determined in the same transition state.