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Regioselective synthesis of multifunctionalised porphyrins-coupling of mono-(pentafluorophenyl)porphyrins to electrophiles

โœ Scribed by Susanna J Shaw; Christine Edwards; Ross W Boyle

Book ID
104262393
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
113 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A method is presented for the coupling of meso-phenylporphyrins, bearing a single pentafluoropbenyl ring, to electrophilic moieties. Selective displacement of the para fluorine atom, using sodium sulphide, results in a transient thiolate species capable of reacting with electrophiles to give a thioether link. A wide range of electrophiles can be used including alkyl iodides, epoxides and activated aromatic systems.

๐Ÿ“œ SIMILAR VOLUMES

Mono-(pentafluorophenyl)porphyrins โ€” use
Mono-(pentafluorophenyl)porphyrins โ€” useful intermediates in the regioselective synthesis of multifunctionalised porphyrins
โœ Susanna J. Shaw; Kerry J. Elgie; Christine Edwards; Ross W. Boyle ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 112 KB

A method is presented for coupling meso-phenylporphyrins bearing a single pentafluorophenyl ring to thiol substituted molecules. Mild reaction conditions are conducive to the employment of a wide range of thiols including biologically active moieties. Both diphenyl-and tetraphenylporphyrins beating