Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 24, Pages 9060-9066Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo701476m
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[Graphics] A procedure was developed for the preparation of beta-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 beta-monofunctionalized porphyrins with various heteroatom functionalities via palladium-mediated carbon-heteroatom bond formations. Examples include beta-amino, -amido, -oxo, and -mercaptoporphyrins from reactions with amines, amides, alcohols, and thiols, respectively. Applying the synthetic approach to chiral amides, beta-chiral porphyrins were effectively constructed.
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