Tributylvinyltin → HCID 178435350, compound

Participants

Reaction Steps

One porphyrin that was not available via this route was the vinyl-porphyrin Zn10, owing to the lack of access to 5-vinyldipyrromethane (vide supra). The synthesis of Zn10 was achieved following the route outlined in Scheme 6. Diacyldipyrromethane 3248 was reduced with NaBH4 and the resulting 32-diol was condensed with dipyrromethane (36)41,49 in CH2Cl2 containing Yb(OTf)3 at room temperature. Subsequent oxidation with DDQ afforded free base porphyrin 37 in 33% yield. Porphyrin 37 was iodinated at the meso-position using I2 and (CF3CO2)2IC6H5 in CHCl3/pyridine50 to furnish free base porphyrin 8 in 82% yield. Zinc insertion afforded Zn8 in 75% yield. Porphyrin Zn8 was then subjected to a Stille cross-coupling reaction51 with (vinyl)tributyltin and Pd(PPh3)4 to afford vinylporphyrin Zn10 in 77% yield.

Provenance & Evidence