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 journalArticle

9 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1776-1779
Number of pages4
JournalOrganic Letters
Volume14
Issue number7
DOIs
StatePublished - Apr 6 2012

Fingerprint

Porphyrins
porphyrins
borohydrides
alkylation
synthesis
reagents
toluene
Borohydrides
vehicles
condensation
chlorides
Alkylation
Toluene
acids
Chlorides
Condensation
Acids
dipyrromethane

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Base-catalyzed direct conversion of dipyrromethanes to 1,9-dicarbinols : A [2 + 2] approach for porphyrins. / Terazono, Yuichi; North, Emily J.; Moore, Ana; Moore, Thomas; Gust, Devens.

In: Organic Letters, Vol. 14, No. 7, 06.04.2012, p. 1776-1779.

Research output: Contribution to journalArticle

@article{07a85a93e5204f388c96269d85e72e7f,
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.",
author = "Yuichi Terazono and North, {Emily J.} and Ana Moore and Thomas Moore and Devens Gust",
year = "2012",
month = "4",
day = "6",
doi = "10.1021/ol300267j",
language = "English (US)",
volume = "14",
pages = "1776--1779",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

T1 - Base-catalyzed direct conversion of dipyrromethanes to 1,9-dicarbinols

T2 - A [2 + 2] approach for porphyrins

AU - Terazono, Yuichi

AU - North, Emily J.

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.

UR - http://www.scopus.com/inward/record.url?scp=84859576033&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84859576033&partnerID=8YFLogxK

U2 - 10.1021/ol300267j

DO - 10.1021/ol300267j

M3 - Article

C2 - 22420376

AN - SCOPUS:84859576033

VL - 14

SP - 1776

EP - 1779

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 7

ER -