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

Yuichi Terazono; Emily J. North; Ana Moore; Thomas Moore; Devens Gust

doi:10.1021/ol300267j

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

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

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1776-1779
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	7
DOIs	https://doi.org/10.1021/ol300267j
State	Published - Apr 6 2012

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - Moore, Ana

AU - Moore, Thomas

AU - Gust, Devens

PY - 2012/4/6

Y1 - 2012/4/6

N2 - 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.

AB - 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.

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

Abstract

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