Suzuki-Miyaura reactions of the bis(triflates) of 1,3- and 1,4-dihydroxythioxanthone. Electronic and steric effects on the site-selectivity

Article abstract of DOI:10.1016/j.tet.2011.10.095

The palladium(0)-catalyzed Suzuki cross-coupling reactions of the bis(triflates) of 1,3- and 1,4-dihydroxythioxanthone afforded various aryl-substituted thioxanthones. While the Suzuki reactions of the bis(triflate) derived from 1,3-dihydroxythioxanthone proceeded by site-selective attack in favor of position 3, the reactions of the bis(triflate) of 1,4- dihydroxythioxanthone proceeded in favor of position 1. The site-selectivity is controlled by steric and electronic parameters.