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Copper-Catalyzed O-Difluoromethylation of Functionalized Aliphatic Alcohols: Access to Complex Organic Molecules with an OCF2H Group

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† Enamine, Ltd., 78 Chervonotkatska str., 02094 Kyiv, Ukraine
‡ Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, Ukraine
§ Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine
⊥ Homogeneous Catalysis and Molecular Design Research Group at Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, PL-90-363 Łódź, Poland
*E-mail: [email protected], [email protected]
*E-mail: [email protected], [email protected]
Cite this: J. Org. Chem. 2016, 81, 14, 5803–5813
Publication Date (Web):May 6, 2016
https://doi.org/10.1021/acs.joc.6b00628
Copyright © 2016 American Chemical Society
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    Abstract

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    A two-step synthetic strategy toward difluoromethyl ethers via a CuI-catalyzed reaction of the alcohols, bearing additional protected functionalities, with FSO2CF2CO2H has been developed. The high potential of the developed protocol has been shown by preparing novel OCF2H-analogues of GABA and l-proline. The described transformation has good functional group compatibility and can serve as a powerful synthetic tool for late-stage preparation of complex OCF2H-containing organic compounds as well as building blocks for drug discovery.

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    35. Mei Zhu, Weijun Fu, Zhiqiang Wang, Chen Xu, Baoming Ji. Visible-light-mediated direct difluoromethylation of alkynoates: synthesis of 3-difluoromethylated coumarins. Organic & Biomolecular Chemistry 2017, 15 (43) , 9057-9060. https://doi.org/10.1039/C7OB02366A
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    37. Kostiantyn Levchenko, Olexandr P. Datsenko, Oleh Serhiichuk, Andrei Tolmachev, Viktor O. Iaroshenko, Pavel K. Mykhailiuk. ChemInform Abstract: Copper‐Catalyzed O‐Difluoromethylation of Functionalized Aliphatic Alcohols: Access to Complex Organic Molecules with an OCF 2 H Group.. ChemInform 2016, 47 (48) https://doi.org/10.1002/chin.201648060
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