Unconventional titania photocatalysis: Direct deployment of carboxylic acids in alkylations and annulations

David W. Manley, Roy T. McBurney, Phillip Miller, Russell F. Howe, Shona Rhydderch, John C. Walton*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

73 Citations (Scopus)

Abstract

Under dry, anaerobic conditions, TiO 2 photocatalysis of carboxylic acid precursors resulted in carbon-carbon bond-forming processes. High yields of dimers were obtained from TiO 2 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 TiO 2 is easily removed by filtration. The anaerobic photocatalysis strategy offers a range of synthetic possibilities.

Original languageEnglish
Pages (from-to)13580-13583
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number33
DOIs
Publication statusPublished - 22 Aug 2012
Externally publishedYes

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