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

Sabrina Bernard (1) , Ramar Arun Kumar (1) , Karine Porte (1) , Pierre Thuéry (2) , Frédéric Taran (1) , Davide Audisio (1)

1 SCBM - Service de Chimie Bio-Organique et de Marquage
2 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

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.

Domains: Chemical Sciences; Material chemistry; Chemical Sciences; Organic chemistry

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, 2018, 2018, pp.2000-2008. ⟨10.1002/ejoc.201800139⟩. ⟨cea-01730661⟩