A visible-light-induced deboronative alkylarylation of acrylamides with organoboronic acids was developed. In this transformation, boronic acids could be activated by the organic photocatalyst of eosin Y, generating alky free radicals in high efficiency. A broad range of substrate scope was examined and a number of 3,3-disubstituted oxindoles were synthesized in high yields.
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Divergent Synthesis of Fluoroalkyl Ketones through Controlling the Reactivity of Organoboronate Complexes.
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The Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, Wuhan 430072, China.
Herein, we report a divergent synthesis of fluoroalkyl ketones through visible-light-induced reactions between readily available organoboronic esters and fluoroalkyl acylsilanes. Selective control of the reactivity of the generated organoboronate complexes is the key to achieving divergent transformations. Under basic conditions, the organoboronate complexes undergo deboronative fluoride elimination, resulting in the formation of enol silyl ethers as intermediates that react with various electrophiles to generate defluorinated ketones as the products.
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Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui 910-8507, Japan.
Visible-light-induced decarboxylative and deboronative reactions using two-molecule organic photoredox catalysts, namely, phenanthrene (Phen) and biphenyl (BP), as electron donors and 9-cyano-10-methoxycarbonylanthracene as an electron acceptor were achieved. The high solubility of significantly improved the reaction efficiency and product yield. In addition, the facile tuning of the oxidation potential of the electron-donor molecule via the replacement of Phen with BP enabled the application of the two-molecule photoredox system to a wide range of substrates.
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Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P.R. China.
A visible-light-induced deboronative alkylarylation of acrylamides with organoboronic acids was developed. In this transformation, boronic acids could be activated by the organic photocatalyst of eosin Y, generating alky free radicals in high efficiency. A broad range of substrate scope was examined and a number of 3,3-disubstituted oxindoles were synthesized in high yields.
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State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
Chemoselective C(sp(3))-C(sp(2)) coupling reactions under mild reaction conditions are useful for synthesizing alkyl-substituted alkenes having sensitive functional groups. Reported here is a visible-light-induced chemoselective alkenylation through a deboronation/decarboxylation sequence under neutral aqueous reaction conditions at room temperature. This reaction represents the first hypervalent-iodine-enabled radical decarboxylative alkenylation reaction, and a novel benziodoxole-vinyl carboxylic acid reaction intermediate was isolated.
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State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032 People's Republic of China.
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