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.