American Chemical Society
ol500569b_si_002.cif (37.67 kB)

Silylethynyl Substituents as Porphyrin Protecting Groups for Solubilization and Selectivity Control

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posted on 2014-03-21, 00:00 authored by Kazuma Oda, Masanari Akita, Satoru Hiroto, Hiroshi Shinokubo
Silylethynyl substituents are proposed as protecting groups for porphyrin derivatives to enhance their solubility and enable regioselective functionalization. After usage as protecting groups, silylethynyl groups at the meso-positions can be efficiently removed upon heating with aqueous H2SO4 in the presence of a surfactant. This approach was applied to the preparation of unsymmetrically β-substituted porphyrins and porphin–porphyrin oligomers, which were inaccessible by conventional methods.