Regioselective ß-silylation of porphyrins via iridium-catalyzed C-H bond activation.

An efficient approach to meso-unsubstituted ß-silylporphyrins was developed through highly regioselective Ir-catalyzed C-H activation, in the presence of HSiMe(OSiMe3)2 as the Si source, from meso-unsubstituted porphyrins. Further transformations of the silyl group, such as oxidation, halogenation, and cross-coupling reactions, could be achieved under mild conditions, demonstrating the synthetic utility of ß-silylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives.