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) |
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Pages (from-to) | 9060-9066 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 72 |
Issue number | 24 |
DOIs | |
State | Published - Nov 23 2007 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry