A Practical Synthesis of Valuable Strained Eight‐Membered‐Ring Derivatives for Click Chemistry

A convenient and cost‐effective synthetic access to cyclooctyne and trans‐cyclooctene derivatives is described. A cyclopropanation step using copper powder in place of Rh2(OAc)4 as catalyst and a symmetric diazomalonate resulted in a drastic decrease in the overall cost of the synthesis. Further der...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-05, Vol.2018 (17), p.2000-2008
Main Authors: Bernard, Sabrina, Kumar, Ramar Arun, Porte, Karine, Thuéry, Pierre, Taran, Frédéric, Audisio, Davide
Format: Article
Language:English
Subjects:
Alkynes
Azides
Chemical synthesis
Click chemistry
Crystallography
Derivatives
Medium‐ring compounds
Strained molecules
Synthetic methods
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Summary:A convenient and cost‐effective synthetic access to cyclooctyne and trans‐cyclooctene derivatives is described. A cyclopropanation step using copper powder in place of Rh2(OAc)4 as catalyst and a symmetric diazomalonate resulted in a drastic decrease in the overall cost of the synthesis. Further derivatizations allowed us to characterize, for the first time, the structure of a BCN analogue by X‐ray crystallography, and to obtain a library of derivatives that could potentially be useful for applications in metal‐free click chemistry. A convenient and cost‐effective synthetic access to cyclooctyne and trans‐cyclooctene derivatives is described. A cyclopropanation step using copper powder in place of Rh2(OAc)4 as catalyst and a symmetric diazomalonate resulted in a drastic decrease in the overall cost of the synthesis.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800139