Direct alkylation of pyrrole with vinyl substituted aromatics: versatile precursors for the synthesis of porphyrinoid macrocycles

Seong Jin Hong; Seung Doo Jeong; Jaeduk Yoo; Jong Seung Kim; Juyoung Yoon; Chang Hee Lee

doi:10.1016/j.tetlet.2008.04.119

Direct alkylation of pyrrole with vinyl substituted aromatics: versatile precursors for the synthesis of porphyrinoid macrocycles

Seong Jin Hong
, Seung Doo Jeong
, Jaeduk Yoo
, Jong Seung Kim
, Juyoung Yoon
, Chang Hee Lee

Department of Chemistry & Nanoscience

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

12 Scopus citations

Abstract

5-Substituted dipyrromethane analogues (8), (23) and (25) were synthesized by the reaction of 2-vinylpyrroles, 2-vinylthiophene or 2-vinylbenzenes with excess pyrrole in the presence of Lewis acids. Accordingly, tripyrromethane analogues could be obtained by starting with 2,5-divinyl thiophene or 2,6-divinylbenzenes. The reaction usually gave moderate yields and catalyst-dependent was seen in some cases. The reaction is compatible with other reported dipyrromethane syntheses and could be applied for the construction of unusual porphyrins.

Original language	English
Pages (from-to)	4138-4141
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.119
State	Published - 23 Jun 2008

Bibliographical note

Funding Information:
This work was supported by a grant from the Korea Science and Engineering Foundation (KOSEF) grant (R01-2006-000-10001-0) funded by the Korean government (MOST). Vascular System Research Center (VSRC) and Central Instrumentation Facility at KNU are acknowledged for support.

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10.1016/j.tetlet.2008.04.119

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title = "Direct alkylation of pyrrole with vinyl substituted aromatics: versatile precursors for the synthesis of porphyrinoid macrocycles",

abstract = "5-Substituted dipyrromethane analogues (8), (23) and (25) were synthesized by the reaction of 2-vinylpyrroles, 2-vinylthiophene or 2-vinylbenzenes with excess pyrrole in the presence of Lewis acids. Accordingly, tripyrromethane analogues could be obtained by starting with 2,5-divinyl thiophene or 2,6-divinylbenzenes. The reaction usually gave moderate yields and catalyst-dependent was seen in some cases. The reaction is compatible with other reported dipyrromethane syntheses and could be applied for the construction of unusual porphyrins.",

author = "Hong, \{Seong Jin\} and Jeong, \{Seung Doo\} and Jaeduk Yoo and Kim, \{Jong Seung\} and Juyoung Yoon and Lee, \{Chang Hee\}",

note = "Funding Information: This work was supported by a grant from the Korea Science and Engineering Foundation (KOSEF) grant (R01-2006-000-10001-0) funded by the Korean government (MOST). Vascular System Research Center (VSRC) and Central Instrumentation Facility at KNU are acknowledged for support.",

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doi = "10.1016/j.tetlet.2008.04.119",

language = "English",

volume = "49",

pages = "4138--4141",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Direct alkylation of pyrrole with vinyl substituted aromatics

T2 - versatile precursors for the synthesis of porphyrinoid macrocycles

AU - Hong, Seong Jin

AU - Jeong, Seung Doo

AU - Yoo, Jaeduk

AU - Kim, Jong Seung

AU - Yoon, Juyoung

AU - Lee, Chang Hee

N1 - Funding Information: This work was supported by a grant from the Korea Science and Engineering Foundation (KOSEF) grant (R01-2006-000-10001-0) funded by the Korean government (MOST). Vascular System Research Center (VSRC) and Central Instrumentation Facility at KNU are acknowledged for support.

PY - 2008/6/23

Y1 - 2008/6/23

N2 - 5-Substituted dipyrromethane analogues (8), (23) and (25) were synthesized by the reaction of 2-vinylpyrroles, 2-vinylthiophene or 2-vinylbenzenes with excess pyrrole in the presence of Lewis acids. Accordingly, tripyrromethane analogues could be obtained by starting with 2,5-divinyl thiophene or 2,6-divinylbenzenes. The reaction usually gave moderate yields and catalyst-dependent was seen in some cases. The reaction is compatible with other reported dipyrromethane syntheses and could be applied for the construction of unusual porphyrins.

AB - 5-Substituted dipyrromethane analogues (8), (23) and (25) were synthesized by the reaction of 2-vinylpyrroles, 2-vinylthiophene or 2-vinylbenzenes with excess pyrrole in the presence of Lewis acids. Accordingly, tripyrromethane analogues could be obtained by starting with 2,5-divinyl thiophene or 2,6-divinylbenzenes. The reaction usually gave moderate yields and catalyst-dependent was seen in some cases. The reaction is compatible with other reported dipyrromethane syntheses and could be applied for the construction of unusual porphyrins.

UR - https://www.scopus.com/pages/publications/44149119018

U2 - 10.1016/j.tetlet.2008.04.119

DO - 10.1016/j.tetlet.2008.04.119

M3 - Article

AN - SCOPUS:44149119018

SN - 0040-4039

VL - 49

SP - 4138

EP - 4141

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Direct alkylation of pyrrole with vinyl substituted aromatics: versatile precursors for the synthesis of porphyrinoid macrocycles

Abstract

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