Synthesis of β-functionalized porphyrins via palladium-catalyzed carbon-heteroatom bond formations: Expedient entry into β-chiral porphyrins

Guang Yao Gao; Joshua V. Ruppel; D. Brett Allen; Ying Chen; X. Peter Zhang

doi:10.1021/jo701476m

Synthesis of β-functionalized porphyrins via palladium-catalyzed carbon-heteroatom bond formations: Expedient entry into β-chiral porphyrins

Guang Yao Gao, Joshua V. Ruppel, D. Brett Allen, Ying Chen, X. Peter Zhang

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

70 Scopus citations

Abstract

(Chemical Equation Presented) A procedure was developed for the preparation of β-monobromo-tetraphenylporphyrin (BrTPP) in a greatly improved yield from the selective bromination of tetraphenylporphyrin (TPP) by NBS. BrTPP was successfully employed as a versatile synthon for convenient synthesis of a wide range of β-monofunctionalized porphyrins with various heteroatom functionalities via palladium-mediated carbon-heteroatom bond formations. Examples include β-amino, -amido, -oxo, and -mercaptoporphyrins from reactions with amines, amides, alcohols, and thiols, respectively. Applying the synthetic approach to chiral amides, β-chiral porphyrins were effectively constructed.

Original language	English (US)
Pages (from-to)	9060-9066
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	72
Issue number	24
DOIs	https://doi.org/10.1021/jo701476m
State	Published - Nov 23 2007
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo701476m

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title = "Synthesis of β-functionalized porphyrins via palladium-catalyzed carbon-heteroatom bond formations: Expedient entry into β-chiral porphyrins",

abstract = "(Chemical Equation Presented) A procedure was developed for the preparation of β-monobromo-tetraphenylporphyrin (BrTPP) in a greatly improved yield from the selective bromination of tetraphenylporphyrin (TPP) by NBS. BrTPP was successfully employed as a versatile synthon for convenient synthesis of a wide range of β-monofunctionalized porphyrins with various heteroatom functionalities via palladium-mediated carbon-heteroatom bond formations. Examples include β-amino, -amido, -oxo, and -mercaptoporphyrins from reactions with amines, amides, alcohols, and thiols, respectively. Applying the synthetic approach to chiral amides, β-chiral porphyrins were effectively constructed.",

author = "Gao, {Guang Yao} and Ruppel, {Joshua V.} and Allen, {D. Brett} and Ying Chen and Zhang, {X. Peter}",

year = "2007",

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doi = "10.1021/jo701476m",

language = "English (US)",

volume = "72",

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journal = "Journal of Organic Chemistry",

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T1 - Synthesis of β-functionalized porphyrins via palladium-catalyzed carbon-heteroatom bond formations

T2 - Expedient entry into β-chiral porphyrins

AU - Gao, Guang Yao

AU - Ruppel, Joshua V.

AU - Allen, D. Brett

AU - Chen, Ying

AU - Zhang, X. Peter

PY - 2007/11/23

Y1 - 2007/11/23

N2 - (Chemical Equation Presented) A procedure was developed for the preparation of β-monobromo-tetraphenylporphyrin (BrTPP) in a greatly improved yield from the selective bromination of tetraphenylporphyrin (TPP) by NBS. BrTPP was successfully employed as a versatile synthon for convenient synthesis of a wide range of β-monofunctionalized porphyrins with various heteroatom functionalities via palladium-mediated carbon-heteroatom bond formations. Examples include β-amino, -amido, -oxo, and -mercaptoporphyrins from reactions with amines, amides, alcohols, and thiols, respectively. Applying the synthetic approach to chiral amides, β-chiral porphyrins were effectively constructed.

AB - (Chemical Equation Presented) A procedure was developed for the preparation of β-monobromo-tetraphenylporphyrin (BrTPP) in a greatly improved yield from the selective bromination of tetraphenylporphyrin (TPP) by NBS. BrTPP was successfully employed as a versatile synthon for convenient synthesis of a wide range of β-monofunctionalized porphyrins with various heteroatom functionalities via palladium-mediated carbon-heteroatom bond formations. Examples include β-amino, -amido, -oxo, and -mercaptoporphyrins from reactions with amines, amides, alcohols, and thiols, respectively. Applying the synthetic approach to chiral amides, β-chiral porphyrins were effectively constructed.

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Synthesis of β-functionalized porphyrins via palladium-catalyzed carbon-heteroatom bond formations: Expedient entry into β-chiral porphyrins

Abstract

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