Base-Catalyzed Direct Conversion of Dipyrromethanes to 1,9-Dicarbinols: A [2 + 2] Approach for Porphyrins

Authors: Terazono, Y., North, E.J., Moore, A.L., Moore, T.A., and Gust, D.
Title: Base-Catalyzed Direct Conversion of Dipyrromethanes to 1,9-Dicarbinols: A [2 + 2] Approach for Porphyrins
Source: Organic Letters
Year: 2012
Volume: 14
Pages: 1776-1779

ABSTRACT:

A variant of the MacDonald approach was devised for the synthesis of porphyrins. A new base-catalyzed one-step synthesis of 1,9-dipyrromethane-dicarbinols was achieved by Friedel- Crafts alkylation of dipyrromethanes using commercially available ethyl glyoxylate solution in toluene. This method avoids the use of acid chlorides, Grignard reagents, borohydride reductions, and acidic conditions. The [2 + 2] condensation of dipyrromethanedicarbinols and dipyrromethanes yielded 5,15-di(ethoxycarbonyl)porphyrins.


Date of online publication: Thu, 2012-03-15
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