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

Sabrina Bernard; Ramar Arun Kumar; Karine Porte; Pierre Thuéry; Frédéric Taran; Davide Audisio

doi:10.1002/ejoc.201800139

Journal articles

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)

NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Material chemistry

Chemical Sciences / Organic chemistry

Complete list of metadatas

https://hal-cea.archives-ouvertes.fr/cea-01730661
Contributor : Serge Palacin <>
Submitted on : Tuesday, March 13, 2018 - 2:41:24 PM
Last modification on : Wednesday, July 8, 2020 - 3:38:21 AM

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

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

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