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Unconventional Titania Photocatalysis: Direct Deployment of Carboxylic Acids in Alkylations and Annulations

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Author(s)

David Manley, Roy Thomas McBurney, Phillip Miller, Russell, F. Howe, Shona Rhydderch, John Christopher Walton

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Abstract

Under dry, anaerobic conditions, TiO2 photocatalysis of carboxylic acid precursors resulted in carbon−carbon bond-forming processes. High yields of
dimers were obtained from TiO2 treatment of carboxylic acids alone. On inclusion of electron-deficient alkenes, efficient alkylations were achieved with methoxymethyl and phenoxymethyl radicals. In reactions with maleic anhydride or maleimides, phenoxyacetic acid produced chromenedione derivatives in addition to adducts. These photocatalytic reactions are simple and cheap to perform, and the TiO2 is easily removed by filtration. The anaerobic photocatalysis strategy offers a range of synthetic possibilities.
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Details

Original languageEnglish
Pages (from-to)13580-13583
JournalJournal of the American Chemical Society
Volume134
Issue number33
Early online date7 Aug 2012
DOIs
StatePublished - 2012

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