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Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes

Phil C. Knutson, Haleigh E. Fredericks, Eric M. Ferreira*

*Department of Chemistry, University of Georgia, Athens, Georgia 30602, United States, Email: emferruga.edu

P. C. Knutson, H. E. Fredericks, E. M. Ferreira, Org. Lett., 2018, 20, 6845-6849.

DOI: 10.1021/acs.orglett.8b02975 (free Supporting Information)



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Abstract

A convenient Cadiot-Chodkiewicz protocol for the use of low molecular weight alkyne coupling partners entails an in situ elimination from a dibromoolefin precursor and immediate subjection to copper-catalyzed conditions. The method circumvents the hazards of volatile brominated alkynes. The internal 1,3-diyne products are evaluated in ruthenium-catalyzed azide-alkyne cycloadditions.

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Key Words

Cadiot-Chodkiewicz Coupling


ID: J54-Y2018