Four new synthetic routes to meso-tetraarylporphyrins using a MacDonald-type 2+ 2 condensation are described. Self-condensation of a 5-'aryldipyrromethane (eg, 17) with an aryl-substituted onecarbon bridging unit affords a mixture of tetraarylporphyrins due to acid- catalyzed redistribution reactions. The second and third methods presented here show wide applicability for the preparation of 5, 10, 15, 20-tetraaryl-substituted porphyrins (eg, 31, 37, ...
[Keifer, Paul A.; Schwartz, Robert E.; Koker, Moustapha E. S.; Hughes, Robert G.; Rittschof, Dan; Rinehart, Kenneth L. Journal of Organic Chemistry, 1991 , vol. 56, # 9 p. 2965 - 2975]