A facile and direct protocol to determine the absolute configurations of chiral mono-alcohols without analyte derivatization can now be realized using a novel circular dichroic (CD)-sensitive bis(zinc porphyrin) BP1 host system. The binding of mono-alcohols to BP1 should be greatly enhanced by the simultaneous double coordination of the hydroxyl group to the two central metals of the porphyrin subunits.

We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH2OH, CH2OMe, and CH2F functionalities and the fluoride ion-mediated desilylative introduction of carbon–carbon single and double bonds.

An efficient one-pot protocol for the direct conversion of free base 5,15-disubstituted porphyrins into the corresponding meso activated alkenyl-substituted meso-formylporphyrins has been developed using a sequential SNAr reaction with PyMe2SiCH2Li, conjugate addition to enones or alkenoates in the presence of TMSCl, and oxidation with DDQ.

The metallophthalocyanine complex Cr(TBPC)OTf works as a highly efficient, recyclable Lewis acid catalyst for the regio- and stereoselective rearrangements of epoxides to aldehydes.

An efficient one-pot procedure which converts 5,15-disubstituted porphyrins into their corresponding mesoacyl-, alkoxycarbonyl-, and carbamoyl-substituted meso-formylporphyrins has been developed, where the procedure involves a sequential SNAr reaction of porphyrins with PyMe2SiCH2Li, followed by acylation or related reactions and oxidation.

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.

A facile and direct protocol to determine the absolute configurations of chiral mono-alcohols without analyte derivatization can now be realized using a novel circular dichroic (CD)-sensitive bis(zinc porphyrin) BP1 host system. The binding of mono-alcohols to BP1 should be greatly enhanced by the simultaneous double coordination of the hydroxyl group to the two central metals of the porphyrin subunits.

The metallophthalocyanine complex Cr(TBPC)OTf works as a highly efficient, recyclable Lewis acid catalyst for the regio- and stereoselective rearrangements of epoxides to aldehydes.

An efficient one-pot procedure which converts 5,15-disubstituted porphyrins into their corresponding mesoacyl-, alkoxycarbonyl-, and carbamoyl-substituted meso-formylporphyrins has been developed, where the procedure involves a sequential SNAr reaction of porphyrins with PyMe2SiCH2Li, followed by acylation or related reactions and oxidation.