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Ruthenium-Catalyzed Azide-Alkyne Cycloaddition: Scope and Mechanism

Brant C. Boren, Sridhar Narayan, Lars K. Rasmussen, Li Zhang, Haitao Zhao, Zhenyang Lin, Guochen Jia and Valery V. Fokin

*Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, Email: fokinscripps.edu

B. C. Boren, S. Narayan, L. K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V. V. Fokin, J. Am. Chem. Soc., 2008, 130, 8923-8930.

DOI: 10.1021/ja0749993 (free Supporting Information)


Abstract

In the presence Cp*RuCl(PPh3)2 or Cp*RuCl(COD) as catalyst, primary and secondary azides react with a broad range of terminal alkynes containing a range of functionalities selectively producing 1,5-disubstituted 1,2,3-triazoles. Both complexes also promote the cycloaddition reactions of organic azides with internal alkynes, providing access to fully-substituted 1,2,3-triazoles.

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proposed mechanism



Ruthenium-Catalyzed Cycloaddition of Aryl Azides and Alkynes

L. K. Rasmussen, B. C. Boren, V. V. Fokin, Org. Lett., 2007, 9, 5337-5339.


Key Words

Click Chemistry, 1,2,3-Triazoles


ID: J48-Y2008-3880