Palladium-mediated synthesis of novel meso-chiral porphyrins: Cobalt-catalyzed cyclopropanation

Ying Chen; Guang Yao Gao; X. Peter Zhang

doi:10.1016/j.tetlet.2005.05.089

Palladium-mediated synthesis of novel meso-chiral porphyrins: Cobalt-catalyzed cyclopropanation

Ying Chen, Guang Yao Gao, X. Peter Zhang

School of Medicine

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

41 Scopus citations

Abstract

A series of novel meso-chiral porphyrins were effectively synthesized from reactions of 5,15-dibromo-10,20-diarylporphyrins with readily available chiral alcohols and amides via palladium-mediated C-N and C-O bond formations. Cobalt complexes of these chiral porphyrins were prepared and shown to be effective catalysts for cyclopropanation of styrene with ethyl diazoacetate under mild and practical conditions, affording the desired cyclopropane ester as a trans-dominant form in excellent yields. Due to orientation and flexibility of the chiral appendages, only low enantioselectivity was observed.

Original language	English (US)
Pages (from-to)	4965-4969
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2005.05.089
State	Published - Jul 25 2005

Keywords

C-N bond formation
C-O bond formation
Chiral porphyrins
Cobalt porphyrins
Cross-coupling
Cyclopropanation
Palladium-catalyzed

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.05.089

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title = "Palladium-mediated synthesis of novel meso-chiral porphyrins: Cobalt-catalyzed cyclopropanation",

abstract = "A series of novel meso-chiral porphyrins were effectively synthesized from reactions of 5,15-dibromo-10,20-diarylporphyrins with readily available chiral alcohols and amides via palladium-mediated C-N and C-O bond formations. Cobalt complexes of these chiral porphyrins were prepared and shown to be effective catalysts for cyclopropanation of styrene with ethyl diazoacetate under mild and practical conditions, affording the desired cyclopropane ester as a trans-dominant form in excellent yields. Due to orientation and flexibility of the chiral appendages, only low enantioselectivity was observed.",

keywords = "C-N bond formation, C-O bond formation, Chiral porphyrins, Cobalt porphyrins, Cross-coupling, Cyclopropanation, Palladium-catalyzed",

author = "Ying Chen and Gao, {Guang Yao} and Zhang, {X. Peter}",

note = "Funding Information: We are grateful for financial support for this work from the UT Department of Chemistry, the UT Center of Excellence for Structural Biology (CESB), Oak Ridge Associated Universities (ORAU) for a Ralph E. Powe Junior Faculty Enhancement Award, Hereditary Disease Foundation (HDF) and High Q Foundation (HQF). ",

year = "2005",

month = jul,

day = "25",

doi = "10.1016/j.tetlet.2005.05.089",

language = "English (US)",

volume = "46",

pages = "4965--4969",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Palladium-mediated synthesis of novel meso-chiral porphyrins

T2 - Cobalt-catalyzed cyclopropanation

AU - Chen, Ying

AU - Gao, Guang Yao

AU - Zhang, X. Peter

N1 - Funding Information: We are grateful for financial support for this work from the UT Department of Chemistry, the UT Center of Excellence for Structural Biology (CESB), Oak Ridge Associated Universities (ORAU) for a Ralph E. Powe Junior Faculty Enhancement Award, Hereditary Disease Foundation (HDF) and High Q Foundation (HQF).

PY - 2005/7/25

Y1 - 2005/7/25

N2 - A series of novel meso-chiral porphyrins were effectively synthesized from reactions of 5,15-dibromo-10,20-diarylporphyrins with readily available chiral alcohols and amides via palladium-mediated C-N and C-O bond formations. Cobalt complexes of these chiral porphyrins were prepared and shown to be effective catalysts for cyclopropanation of styrene with ethyl diazoacetate under mild and practical conditions, affording the desired cyclopropane ester as a trans-dominant form in excellent yields. Due to orientation and flexibility of the chiral appendages, only low enantioselectivity was observed.

AB - A series of novel meso-chiral porphyrins were effectively synthesized from reactions of 5,15-dibromo-10,20-diarylporphyrins with readily available chiral alcohols and amides via palladium-mediated C-N and C-O bond formations. Cobalt complexes of these chiral porphyrins were prepared and shown to be effective catalysts for cyclopropanation of styrene with ethyl diazoacetate under mild and practical conditions, affording the desired cyclopropane ester as a trans-dominant form in excellent yields. Due to orientation and flexibility of the chiral appendages, only low enantioselectivity was observed.

KW - C-N bond formation

KW - C-O bond formation

KW - Chiral porphyrins

KW - Cobalt porphyrins

KW - Cross-coupling

KW - Cyclopropanation

KW - Palladium-catalyzed

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U2 - 10.1016/j.tetlet.2005.05.089

DO - 10.1016/j.tetlet.2005.05.089

M3 - Article

AN - SCOPUS:20544475275

SN - 0040-4039

VL - 46

SP - 4965

EP - 4969

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Palladium-mediated synthesis of novel meso-chiral porphyrins: Cobalt-catalyzed cyclopropanation

Abstract

Keywords

ASJC Scopus subject areas

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