Meso-tetraarylporphyrins (14 examples) are prepared efficiently by condensation of pyrrole with aromatic aldehydes in the presence of silica chloride, followed by air oxidation. The method is compared with other published procedures.
(a) FielR.J., MusserD. A., MarkE. H., MazurchukR., and AllettoJ., J. Magn. Reson. Imaging1990, 8, 252; (b) J. Ding,; Balzarin, Biochem. Pharmacol. 1992, 44, 80, 1675.
2.
For a review, see MlodnickaT., J. Mol. Catal.1986, 36, 205.
3.
SharghiH., and NaeimiH., J. Chem. Res.1999, 310
4.
LindseyJ.S., SchreimanI. C., HsuH. C., KearneyP. C., and MarguerettazA. M., J. Org. Chem.1987, 52, 827.
5.
Bonar-LawR.P., J. Org. Chem., 1996, 61, 3623.
6.
LindseyJ.S., YangK., and LiF., Tetrahedron1997, 53, 12339.
7.
GeierG.R., CirighY., LiF., HaynesD. M., and LindseyJ. S., Organic Lett., 2000, 2, 1745.
8.
OnakaM., ShinodaT., IzumiY., and NolenE., Tetrahedron Lett.1993, 34, 2625.
9.
ShinodaT., IzumiY., and OnakaM., J. Chem. Soc., Chem. Commun., 1995, 1801.
10.
DrainC.M., and GongX., Chem. Commun., 1997, 2117.
11.
AdlerA.D., LongoF. R., FinarelliJ. D., GolldmacherJ., AssourJ., and KorsakoffL., J. Org. Chem., 1976, 32, 476; (b) F.R. Longo, J.D. Finarelli and J. Kim, J. Heterocyclic Chem., 1969, 6, 927; (c) A.R. Adler, F.R. Longo, F. Kampas and J. Kim, J. Inorg. Nucl. Chem., 1970, 32, 2443.
12.
Rocha GonsalvesA.M., and VarejaoJ. M. M., J. Heterocycl. Chem., 1991, 28, 635.
13.
CornellisA., and LaszloP., Synlett1994, 155; (b) A. McKillop and D. W. Young, Synthesis 1979, 401 and 481; (c) P. Laszlo, Preparative Chemistry Using Supported Reagents, Academic Press, San Diego, 1987. (d) P. Laszlo and A. Cornellis, Aldrichimica Acta 1988, 21, 97.
14.
FirouzabadiH., IranpoorN., KarimiB., and HazarkhaniH., Synlett, 2000, 263.
15.
MamardashuliM. Zh., and GolubchikovO. A., Russ. Chem., Rev.2001, 70, 577.
16.
GradillasA., and CampoC., SinisterraJ., and LiamaF. J., Chem. Soc. Perkin Trans. 1, 1995, 2611.
