Pentafluorophenyl Transfer:  A New Group-Transfer Reaction in Organoborate Salts

Irradiation of isoquinolinium hydroxytris(pentafluorophenyl)borate, 1, and phenanthridium hydroxytris(pentafluorophenyl)borate, 2, in either CH₂Cl₂ or CH₃CN resulted in C₆F₅ transfer to the isoquinolinium and phenanthridium cations, generating 2-methyl-1-(2,3,4,5,6- pentafluorophenyl)-1,2-dihydroisoquinoline, 3, and 2-methyl-1-(2,3,4,5,6-pentafluorophenyl)-1,2-dihydrophenanthridine, 4, respectively. In addition, photogeneration of H₂O·B(C₆F₅)₃ resulted from 1. Photogeneration of C₆F₅−C₆F₄H from HO−B(C₆F₅)₃^- and of C₆H₅−C₆F₄H from C₆H₅−B(C₆F₅)₃^- was discovered.