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Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from Terminal Alkynes

José Ramón Suárez, Daniel Collado-Sanz, Diego J. Cárdenas and Jose Luis Chiara*

*Instituto de Química Orgánica General (IQOG-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain, Email: jl.chiaracsic.es

J. R. Suárez, D. Collado-Sanz, D. J. Cárdenas, J. L. Chiara, J. Org. Chem., 2015, 80, 1098-1106.

DOI: 10.1021/jo5025909 (free Supporting Information)



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Abstract

Nonafluorobutanesulfonyl azide is a highly efficient reagent for an extremely fast copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. In addition, nonafluorobutanesulfonyl azide is a superior and safe alternative to other electrophilic azide reagents in use today.

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Key Words

1,3-Diynes, Nonafluorobutanesulfonyl Azide


ID: J42-Y2015