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 journalArticle

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 languageEnglish (US)
Pages (from-to)9060-9066
Number of pages7
JournalJournal of Organic Chemistry
Volume72
Issue number24
DOIs
StatePublished - Nov 23 2007

ASJC Scopus subject areas

  • Organic Chemistry

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