A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4,7-dihydroisoindole

Mikhail A. Filatov; Andrei V. Cheprakov; Irina P. Beletskaya

doi:10.1002/ejoc.200700014

A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4,7-dihydroisoindole

Mikhail A. Filatov, Andrei V. Cheprakov, Irina P. Beletskaya

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

Abstract

A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of the aromatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capabilities of the new method are illustrated by the synthesis of meso- tetraaryltetrabenzoporphyrins, as well as the first unambiguous synthesis and characterization of 5,15-diphenyltetrabenzoporphyrin.

Original language	English
Pages (from-to)	3468-3475
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	21
DOIs	https://doi.org/10.1002/ejoc.200700014
Publication status	Published - 2007
Externally published	Yes

Keywords

π-extended porphyrins
Dipyrromethanes
Nitrogen heterocycles
Porphyrinoids
Tetrabenzoporphyrins

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10.1002/ejoc.200700014

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title = "A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4,7-dihydroisoindole",

abstract = "A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of the aromatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capabilities of the new method are illustrated by the synthesis of meso- tetraaryltetrabenzoporphyrins, as well as the first unambiguous synthesis and characterization of 5,15-diphenyltetrabenzoporphyrin.",

keywords = "π-extended porphyrins, Dipyrromethanes, Nitrogen heterocycles, Porphyrinoids, Tetrabenzoporphyrins",

author = "Filatov, \{Mikhail A.\} and Cheprakov, \{Andrei V.\} and Beletskaya, \{Irina P.\}",

year = "2007",

doi = "10.1002/ejoc.200700014",

language = "English",

pages = "3468--3475",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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T1 - A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4,7-dihydroisoindole

AU - Filatov, Mikhail A.

AU - Cheprakov, Andrei V.

AU - Beletskaya, Irina P.

PY - 2007

Y1 - 2007

N2 - A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of the aromatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capabilities of the new method are illustrated by the synthesis of meso- tetraaryltetrabenzoporphyrins, as well as the first unambiguous synthesis and characterization of 5,15-diphenyltetrabenzoporphyrin.

AB - A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of the aromatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capabilities of the new method are illustrated by the synthesis of meso- tetraaryltetrabenzoporphyrins, as well as the first unambiguous synthesis and characterization of 5,15-diphenyltetrabenzoporphyrin.

KW - π-extended porphyrins

KW - Dipyrromethanes

KW - Nitrogen heterocycles

KW - Porphyrinoids

KW - Tetrabenzoporphyrins

UR - https://www.scopus.com/pages/publications/34447571836

U2 - 10.1002/ejoc.200700014

DO - 10.1002/ejoc.200700014

M3 - Article

AN - SCOPUS:34447571836

SN - 1434-193X

SP - 3468

EP - 3475

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 21

ER -

A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4,7-dihydroisoindole

Abstract

Keywords

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