Pentafluorophenyl transfer: a new group-transfer reaction in organoborate salts.
[reaction: see text] 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 x 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.
Hewavitharanage
Priyadarshine
P
Center for Photochemical Sciences, Bowling Green State University, Bowling Green, Ohio 43403, USA.
Danilov
Evgeny O
EO
Neckers
Douglas C
DC