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■ Syntheses of Regiospecifically Meso Functionalized Dipyrromethanes, Porphyrins, and Diphenylethane-linked Bisporphyrins

David A. Lee, Jean M. Brisson, and Kevin M. Smith*

*Department of Chemistry, University of California, One Shields Ave., Davis, CA 95616, U.S.A.

Abstract

Acid catalyzed condensation of 2-unsubstituted pyrroles with diethyl acetals permits preparation, in good yields, of a variety of meso-functionalized dipyrromethanes. Subsequent use in the so-called MacDonald “2+2” condensation provides 5-functionalized porphyrins and, eventually, benzochlorin derivatives. A novel application of a reductive coupling scheme, utilizing Ni(0), provides diphenylethane-linked bisporphyrins, which are potential models for electron transfer studies.