Abstract
This review presents the most recent developments on the synthesis of dipyrromethanes, covering classical synthetic strategies, using acid catalyzed condensation of pyrroles and aldehydes or ketones, and recent breakthroughs which allow the synthesis of these type of heterocycles with new substitution patterns.
Highlights
Dipyrromethanes are well known synthetic scaffolds for the synthesis of macrocycles and dipyrromethene metal complexes
Dipyrromethanes occupy a central place in porphyrin chemistry
The dipyrromethane structures employed in the synthesis of naturally occurring porphyrins typically bear substituents at the β-positions and lack any substituent at the meso-position
Summary
Dipyrromethanes are well known synthetic scaffolds for the synthesis of macrocycles and dipyrromethene metal complexes. The dipyrromethanes with substituents at the meso-position have come to play a valuable role in the preparation of synthetic porphyrins [1,2], calixpyrroles [3], chlorins [4], corroles [5], and expanded porphyrins, namely saphyrins and smaragdyrins [6,7] (Figure 1). The synthetic strategies have been organized in two main approaches: classical synthetic strategies based on the first report on the synthesis of meso-substituted dipyrromethanes, disclosed in 1974 [33], using acid catalyzed condensation of pyrrole and aldehydes; and recent breakthroughs in dipyrromethane chemistry which allow the synthesis of dipyrromethanes with new substitution patterns
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