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Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation

Arnold, Dennis, Bottle, Steven, Johnson, Therese, & Keddie, Daniel (2005) Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation. Organic and Biomolecular Chemistry, 3, pp. 2593-2598.

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Abstract

The synthesis of a new structural class of isoindoline nitroxides (aminoxyls), accessible via the palladium-catalysed Heck reaction, is presented. Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analogous bromonitroxides 6 and 7 with methyl acrylate gives the acrylate substituted tetramethylisoindoline amines 8 and 10 and nitroxides 12 and 14. Similarly, the reaction of the aryl bromides and dibromides 4–7 with methyl 4-vinylbenzoate gives the carboxystyryl substituted tetramethylisoindoline amines 9 and 11 and the analogous nitroxides 13 and 15. The carboxystyryl tetramethylisoindoline nitroxides demonstrate strongly suppressed fluorescence, which is revealed upon removal of the free radical by reduction or radical coupling.

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16 citations in Web of Science®

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ID Code: 23836
Item Type: Journal Article
Keywords: Nitroxides, Palladium, Heck Reaction
DOI: 10.1039/B504354A
ISSN: 1477-0520
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > MEDICINAL AND BIOMOLECULAR CHEMISTRY (030400)
Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500)
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Deposited On: 18 Jun 2009 00:10
Last Modified: 29 Feb 2012 23:12

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