Base-catalyzed direct conversion of dipyrromethanes to 1,9-dicarbinols: A [2 + 2] approach for porphyrins

Yuichi Terazono, Emily J. North, Ana L. Moore, Thomas A. Moore, Devens Gust

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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.

Original languageEnglish
Pages (from-to)1776-1779
Number of pages4
JournalOrganic Letters
Issue number7
Publication statusPublished - Apr 6 2012


ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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