Regioselective β-silylation of porphyrins via iridium-catalyzed C–H bond activation?

Organic & Biomolecular Chemistry Pub Date: 2016-10-21 DOI: 10.1039/C6OB02243J

Abstract

An efficient approach to meso-unsubstituted β-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 β-silylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives.

Graphical abstract: Regioselective β-silylation of porphyrins via iridium-catalyzed C–H bond activation
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