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

doi:10.1021/ja306168h

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 journal › Article › peer-review

104 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 language	English
Pages (from-to)	13580-13583
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	33
DOIs	https://doi.org/10.1021/ja306168h
Publication status	Published - 22 Aug 2012
Externally published	Yes

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title = "Unconventional titania photocatalysis: Direct deployment of carboxylic acids in alkylations and annulations",

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.",

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T1 - Unconventional titania photocatalysis

T2 - Direct deployment of carboxylic acids in alkylations and annulations

AU - Manley, David W.

AU - McBurney, Roy T.

AU - Miller, Phillip

AU - Howe, Russell F.

AU - Rhydderch, Shona

AU - Walton, John C.

PY - 2012/8/22

Y1 - 2012/8/22

N2 - 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.

AB - 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.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 33

ER -

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

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