Porphyrin meso-tetra series

R. Bonnett, R.D. White, U.J. Winfield, M.C. Berenbaum (1989). Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumor photosensitizers. Biochem. J., 261, 277-280. 

Shinkai et al. have used a different methodology to prepare a series of meso-tetra-glycoarylporphyrin derivatives 64-67 [97-99]. The sugar-appended porphyrin compounds, 64a-67a were synthesized in accordance with Scheme 10. The target compounds were obtained after deprotection of the hydroxyl groups of porphyrin precursors 64b-67b. These were prepared from the condensation of aminophenyl-2,3,4,6-tetra-0-acetyl-monosaccharide 63(o,p) with the acid-chloride derivative 62 [99]. 

Fig. 7.15 A selection of porphyrins and reduced porphyrins in the meso-tetra (hydroxyphenyl) series. [After Bonnett et al. and Milgrom.]...

A series of osmium meso-tetra-p-tolyl-porphyrin carbene complexes, (TTP) Os(CRR )(R,R = p-tolyl R = H, R = SiMe3 or C02Et) were first prepared by Woo and Smith [ 149] by treating [(TTP)20s] with the appropriate diazoalkanes (Eq. 19). As an indirect method, one of these carbene complexes can also be prepared by reaction of the silylene complex (TTP)Os(SiEt2)(THF) (150) with di-p-tolyl diazomethane. 

The Zaworotko group used meso-tetra(N-methyl-4-pyridyl)porphyrin tetratosylate (TMPyP) as template to construct a series of metal-organic materials (MOMs)... 

The eclipsed tetra-BINAP porphyrin 171 was conveniently synthesized by condensation of the meso-tetrakis(2,6-dihydroxyphenyl)porphyrin 173 with the (S)-BINAP derivative 174 in the presence of K2C03. After removal of the staggered isomer iron was inserted by addition of Fe(CO)5/I2, and the resulting Fe(III)-complex 171 was used as a catalyst (0.2%) to epoxidize a series of six styrene derivatives in the presence of an excess of PhIO. In every case the corresponding (R)-epoxides were preferentially formed in yields up to 72%. The best ee-values were obtained for the electron deficient substrates 2-nitrostyrene (80% ee) and pentafluorostyrene (74% ee), [114],... 

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