First examples of functionalisation of meso-aryl tetrabenzotriazaporphyrins (TBTAPs) through cross-coupling reactions

Nuha Alharbi; Graham J. Tizzard; S. J. Coles; Mike Cook; Andy Cammidge

doi:10.1016/j.tet.2015.03.095

First examples of functionalisation of meso-aryl tetrabenzotriazaporphyrins (TBTAPs) through cross-coupling reactions

Nuha Alharbi, Graham J. Tizzard, S. J. Coles, Mike Cook, Andy Cammidge (Lead Author)

Synthetic and Medicinal Chemistry

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

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Abstract

Recent synthetic advances have given convenient access to tetrabenzotriazaporphyrins (TBTAPs) functionalised with meso-aryl substituents. In this paper we report the first examples of further functionalization of the meso-sites through Suzuki-Miyaura and copper-free Sonagashira cross-coupling reactions of the meso-(bromophenyl)TBTAPs, demonstrating the breadth of new materials design now possible in the hybrid macrocycles.

Original language	English
Pages (from-to)	7227–7232
Number of pages	6
Journal	Tetrahedron
Volume	71
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2015.03.095
Publication status	Published - 30 Sept 2015

Keywords

Phthalocyanines
Porphyrins
Heterocycles
Synthesis
Hybrids
Cross-Coupling

Access to Document

10.1016/j.tet.2015.03.095

KATRITZKY TBTAP TETRAHEDRON 2015 FINALAccepted author manuscript, 196 KBLicence: CC BY-NC-ND

Cite this

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title = "First examples of functionalisation of meso-aryl tetrabenzotriazaporphyrins (TBTAPs) through cross-coupling reactions",

abstract = "Recent synthetic advances have given convenient access to tetrabenzotriazaporphyrins (TBTAPs) functionalised with meso-aryl substituents. In this paper we report the first examples of further functionalization of the meso-sites through Suzuki-Miyaura and copper-free Sonagashira cross-coupling reactions of the meso-(bromophenyl)TBTAPs, demonstrating the breadth of new materials design now possible in the hybrid macrocycles. ",

keywords = "Phthalocyanines, Porphyrins, Heterocycles, Synthesis, Hybrids, Cross-Coupling",

author = "Nuha Alharbi and Tizzard, {Graham J.} and Coles, {S. J.} and Mike Cook and Andy Cammidge",

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T1 - First examples of functionalisation of meso-aryl tetrabenzotriazaporphyrins (TBTAPs) through cross-coupling reactions

AU - Alharbi, Nuha

AU - Tizzard, Graham J.

AU - Coles, S. J.

AU - Cook, Mike

AU - Cammidge, Andy

PY - 2015/9/30

Y1 - 2015/9/30

N2 - Recent synthetic advances have given convenient access to tetrabenzotriazaporphyrins (TBTAPs) functionalised with meso-aryl substituents. In this paper we report the first examples of further functionalization of the meso-sites through Suzuki-Miyaura and copper-free Sonagashira cross-coupling reactions of the meso-(bromophenyl)TBTAPs, demonstrating the breadth of new materials design now possible in the hybrid macrocycles.

AB - Recent synthetic advances have given convenient access to tetrabenzotriazaporphyrins (TBTAPs) functionalised with meso-aryl substituents. In this paper we report the first examples of further functionalization of the meso-sites through Suzuki-Miyaura and copper-free Sonagashira cross-coupling reactions of the meso-(bromophenyl)TBTAPs, demonstrating the breadth of new materials design now possible in the hybrid macrocycles.

KW - Phthalocyanines

KW - Porphyrins

KW - Heterocycles

KW - Synthesis

KW - Hybrids

KW - Cross-Coupling

U2 - 10.1016/j.tet.2015.03.095

DO - 10.1016/j.tet.2015.03.095

M3 - Article

SN - 0040-4020

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SP - 7227

EP - 7232

JO - Tetrahedron

JF - Tetrahedron

IS - 39

ER -