title: Base-catalyzed direct conversion of dipyrromethanes to 1,9-dicarbinols: a [2 + 2] approach for porphyrins.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Center for Bio-Inspired Solar Fuel Production, Arizona State University, Tempe, Arizona 85287-1604, USA.
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Terazono
authors.forename: Emily J
authors.initials: EJ
authors.lastname: North
authors.forename: Ana L
authors.initials: AL
authors.lastname: Moore
authors.forename: Thomas A
authors.initials: TA
authors.lastname: Moore
authors.forename: Devens
authors.initials: D
authors.lastname: Gust
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D011166:Porphyrins; D011758:Pyrroles; C512015:dipyrromethane