[(NHC)2Cu]X Complexes as Efficient Catalysts for Azide–Alkyne Click Chemistry at Low Catalyst Loadings†
Silvia Díez-González Dr.
Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain), Fax: (+34) 977-920-244 http://www.iciq.es/english/research/grups_eng/nolan/entrada.htm
Search for more papers by this authorSteven P. Nolan Prof. Dr.
Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain), Fax: (+34) 977-920-244 http://www.iciq.es/english/research/grups_eng/nolan/entrada.htm
Search for more papers by this authorSilvia Díez-González Dr.
Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain), Fax: (+34) 977-920-244 http://www.iciq.es/english/research/grups_eng/nolan/entrada.htm
Search for more papers by this authorSteven P. Nolan Prof. Dr.
Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain), Fax: (+34) 977-920-244 http://www.iciq.es/english/research/grups_eng/nolan/entrada.htm
Search for more papers by this authorThe ICIQ Foundation and the Spanish Ministerio de Educación y Ciencia are gratefully acknowledged for financial support. S.D.G. thanks the MEC for financial support through the Torres Quevedo program. S.P.N. is an ICREA Research Professor. We thank Dr. Nicolas “La Click, c'est chic” Marion for insightful reading of this manuscript. NHC=N-heterocyclic carbene.
Graphical Abstract
La click, c'est chic! A catalytic system based on an [(NHC)2Cu]X complex (NHC=N-heterocyclic carbene) was developed for the [3+2] cycloaddition of azides with alkynes under click conditions (see scheme). This system is broad in scope and highly efficient (turnover frequencies up to 5000 h−1) even at very low catalyst loadings (down to 40 ppm). Preliminary mechanistic studies suggest a specific precatalyst-activation pathway.
Supporting Information
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