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

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• 作者：David W. Manley ; Roy T. McBurney ; Phillip Miller ; Russell F. Howe ; Shona Rhydderch ; John C. Walton
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：August 22, 2012
• 年：2012
• 卷：134
• 期：33
• 页码：13580-13583
• 全文大小：243K
• 年卷期：v.134,no.33(August 22, 2012)
• ISSN：1520-5126

文摘

Under dry, anaerobic conditions, TiO₂ photocatalysis of carboxylic acid precursors resulted in carbon鈥揷arbon 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.