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syn-Fluoro- and -Oxy-trifluoromethylation of Arylacetylenes

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journal contribution
posted on 18.11.2017, 13:48 by Song-Lin Zhang, Hai-Xing Wan, Wen-Feng Bie
One-step concurrent fluoro-trifluoromethylation across the triple bond of arylacetylenes in a syn mode is enabled by the collaboration of (phen)­CuIII(CF3)3 and CsF that produces chemo-, regio-, and stereoselectively (Z)-α-fluoro-β-CF3 styrenes. This method can be extended to achieve syn-oxy-trifluoromethylation and syn-aryl-trifluoromethylation of alkynes using phenoxides, alkoxides, or phenylboronic acid in place of CsF. It opens up new opportunities for preparing various functionalized trifluoromethylated Z-alkenes and demonstrates the potential of Cu­(III)–CF3 complexes in organic synthesis.