Photoheterolysis of aryl halides substituted with electron-donating groups (EDGs) or aryl esters in 2,2,2-trifluoroethanol (TFE) leads to phenyl cations, which can add to alkynes (see scheme, Tf=trifluoromethanesulfonyl). This reaction is an appealing metal-free alternative to the (sila)-Sonogashira reaction.
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Protti et al. (2005) studied this question.
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