We have developed a number of new fluorination1,2 and trifluoromethylation3-5 reactions based on benziodoxole reagents 1a and 1b. The reactions were carried out in the presence of copper, palladium, zinc or silver mediators/catalysts. The reactions are highly regio- and stereoselective. The presentation will be mainly focused on fluorination reactions with 1a.1,2 However, we will point out the mechanistic similarities between the metal assisted activation of 1a and 1b. (1) Ilchenko, N. O.; Tasch, B. O. A.; Szabó, K. J. Angew. Chem. Int. Ed. 2014, 53, 12897. (2) Yuan, W.; Szabó, K. J. Angew. Chem. Int. Ed. 2015, 54, 8533. (3) Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882. (4) Ilchenko, N. O.; Janson, P. G.; Szabo, K. J. J. Org. Chem. 2013, 78, 11087. (5) Ilchenko, N. O.; Janson, P. G.; Szabó, K. J. Chem. Commun. 2013, 49, 6614.

Metal mediated fluorination with fluoro-benziodoxole reagents

251st National Meeting (2016)

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