A practical synthesis of valuable strained 8-membered ring derivatives for click chemistry

Abstract : A convenient and cost-effective synthetic access to cyclooctyne and trans-cyclooctene derivatives is described. A cyclopropanation step using copper powder in lieu of Rh₂(OAc)₄ as catalyst and a symmetric diazomalonate enabled to drastically reduce the overall cost of the synthesis. Further derivatizations allowed to characterize, for the first time, the structure of a BCN analogue by X-ray crystallography and obtain a library of derivatives potentially useful for applications in metal free click chemistry.
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https://hal-cea.archives-ouvertes.fr/cea-01730661
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Submitted on : Tuesday, March 13, 2018 - 2:41:24 PM
Last modification on : Thursday, March 7, 2019 - 3:34:14 PM

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Sabrina Bernard, Ramar Arun Kumar, Karine Porte, Pierre Thuéry, Frédéric Taran, et al.. A practical synthesis of valuable strained 8-membered ring derivatives for click chemistry. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, 2018, pp.2000-2008. ⟨http://dx.doi.org/10.1002/ejoc.201800139⟩. ⟨10.1002/ejoc.201800139⟩. ⟨cea-01730661⟩

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