Skip to content

Research at St Andrews

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

Research output: Research - peer-reviewArticle

DOI

Author(s)

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

School/Research organisations

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.
Close

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

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Microhydration and the enhanced acidity of free radicals

    Walton, J. C. 14 Feb 2018 In : Molecules. 23, 2, 423

    Research output: Research - peer-reviewArticle

  2. Enhanced proton loss from neutral free radicals: toward carbon-centered superacids

    Walton, J. C. 8 Feb 2018 In : Journal of Physical Chemistry A. 122, 5, p. 1422-1431 10 p.

    Research output: Research - peer-reviewArticle

  3. Dealkanative main group couplings across the peri-gap

    Taylor, L. J., Buehl, M., Chalmers, B. A., Ray, M. J., Wawrzyniak, P., Walton, J. C., Cordes, D. B., Slawin, A. M. Z., Woollins, J. D. & Kilian, P. 27 Dec 2017 In : Journal of the American Chemical Society. 139, 51, p. 18545-18551

    Research output: Research - peer-reviewArticle

  4. Generation and structure of unique boriranyl radicals

    Walton, J. C., McFadden, T. R. & Curran, D. P. 22 Nov 2017 In : Journal of the American Chemical Society. 139, 46, p. 16514-16517

    Research output: Research - peer-reviewArticle

  5. N- to C-sulfonyl photoisomerisation of dihydropyridinones: a synthetic and mechanistic study

    Yeh, P-P., Taylor, J. E., Stark, D. G., Daniels, D. S. B., Fallan, C., Walton, J. C. & Smith, A. D. 16 Oct 2017 In : Organic & Biomolecular Chemistry. 15, 42, p. 8914-8922

    Research output: Research - peer-reviewArticle

Related by journal

  1. An environmentally-responsive reciprocal replicating network

    Robertson, C. C., Mackenzie, H. W., Kosikova, T. & Philp, D. 6 Jun 2018 In : Journal of the American Chemical Society. 140, 22, p. 6832-6841 10 p.

    Research output: Research - peer-reviewArticle

  2. Distance measurement of a non-covalently bound Y@C82 Pair with double electron electron resonance spectroscopy

    Gil-Ramírez, G., Shah, A., El Mkami, H., Porfyrakis, K., Briggs, A. D., Morton, J. J. L., Anderson, H. L. & Lovett, J. E. 6 Jun 2018 (Accepted/In press) In : Journal of the American Chemical Society. Just Accepted

    Research output: Research - peer-reviewArticle

  3. A structural model of a P450-ferredoxin complex from orientation-selective double electron-electron resonance spectroscopy

    Bowen, A. M., Johnson, E. O. D., Mercuri, F., Hoskins, N. J., Qiao, R., McCullagh, J. S. O., Lovett, J. E., Bell, S. G., Zhou, W., Timmel, C. R., Wong, L. L. & Harmer, J. R. 21 Feb 2018 In : Journal of the American Chemical Society. 140, 7, p. 2514-2527

    Research output: Research - peer-reviewArticle

  4. Interrogating Pd(II) anion metathesis using a bifunctional chemical probe

    Molloy, J. J., Seath, C. P., West, M. J., McLaughlin, C., Fazakerley, N. J., Kennedy, A. R., Nelson, D. J. & Watson, A. J. B. 10 Jan 2018 In : Journal of the American Chemical Society. 140, 1, p. 126-130

    Research output: Research - peer-reviewArticle

  5. Dealkanative main group couplings across the peri-gap

    Taylor, L. J., Buehl, M., Chalmers, B. A., Ray, M. J., Wawrzyniak, P., Walton, J. C., Cordes, D. B., Slawin, A. M. Z., Woollins, J. D. & Kilian, P. 27 Dec 2017 In : Journal of the American Chemical Society. 139, 51, p. 18545-18551

    Research output: Research - peer-reviewArticle

Related by journal

  1. Journal of the American Chemical Society (Journal)

    David Trevor Richens (Editor)
    2005 → …

    Activity: Publication peer-review and editorial workEditor of research journal

ID: 26628725