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Org Lett. 2014 Mar 21;16(6):1818-21. doi: 10.1021/ol500569b. Epub 2014 Mar 3.

Silylethynyl substituents as porphyrin protecting groups for solubilization and selectivity control.

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  • 1Department of Applied Chemistry, Graduate School of Engineering, Nagoya University , Nagoya, 464-8603, Japan.


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.

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