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Title: The palladium-catalysed copper-free Sonogashira coupling of isoindoline nitroxides: a convenient route to robust profluorescent carbon-carbon frameworks
Contributor(s): Keddie, Daniel  (author); Fairfull-Smith, Kathryn (author); Bottle, Steven E (author)
Publication Date: 2008
DOI: 10.1039/b806963h
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Abstract: A series of novel acetylene-substituted isoindoline nitroxides were synthesised via palladium-catalysed copper-free Sonogashira coupling. These results demonstrate that the Sonogashira reaction is suitable for the generation of a wide range of aryl nitroxides of expanded structural variety. The novel aryl-iodide containing nitroxide, 5-iodo-1,1,3,3-tetramethylisoindolin-2-yloxyl, 3, was a key intermediate for this coupling, giving acetylene-substituted isoindoline nitroxides in high yield. Subsequent reaction of the deprotected ethynyl nitroxide 12 with iodinated polyaromatics furnished novel aromatic nitroxides with extended-conjugation. Such nitroxides have been described as profluorescent, as their quantum yields are significantly lower than those of the corresponding diamagnetic derivatives. The quantum yields of the naphthyl- and phenanthryl-acetylene isoindoline nitroxides (13 and 14) were found to be ~200-fold and ~65-fold less than the non-radical methoxyamine derivatives (23 and 24). Ethyne- and butadiyne-linked nitroxide dimers could also be synthesised by this cross coupling methodology.
Publication Type: Journal Article
Grant Details: ARC/CE0561607
Source of Publication: Organic & Biomolecular Chemistry, v.6, p. 3135-3143
Publisher: RSC Publications
Place of Publication: United Kingdom
ISSN: 1477-0520
Field of Research (FOR): 030503 Organic Chemical Synthesis
030501 Free Radical Chemistry
Socio-Economic Outcome Codes: 970103 Expanding Knowledge in the Chemical Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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