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A Valuable, Inexpensive CuI/N-Heterocyclic Carbene Catalyst for the Selective Diboration of Styrene

Authors

  • Vanesa Lillo,

    1. Dpt. Química Física i Inorgànica, Universitat Rovira i Virgili, Marcel.lí Domingo s/n, 43007 Tarragona, Spain, Fax: (+34) 977-55-95-63
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  • Manuel R. Fructos,

    1. Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al CSIC, Universidad de Huelva, Campus de El Carmen, 21007-Huelva, Spain, Fax: (+34) 959-219942
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  • Jesús Ramírez,

    1. Dpt. Química Física i Inorgànica, Universitat Rovira i Virgili, Marcel.lí Domingo s/n, 43007 Tarragona, Spain, Fax: (+34) 977-55-95-63
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  • Ataualpa A. C. Braga,

    1. Institute of Chemical Research of Catalonia (ICIQ), 43007 Tarragona, Catalonia, Spain
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  • Feliu Maseras Dr.,

    1. Institute of Chemical Research of Catalonia (ICIQ), 43007 Tarragona, Catalonia, Spain
    2. Unitat de Química Física, Universitat Autònoma de Barcelona, 08193 Bellaterra, Catalonia, Spain
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  • M. Mar Díaz-Requejo Dr.,

    1. Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al CSIC, Universidad de Huelva, Campus de El Carmen, 21007-Huelva, Spain, Fax: (+34) 959-219942
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  • Pedro J. Pérez Prof.,

    1. Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al CSIC, Universidad de Huelva, Campus de El Carmen, 21007-Huelva, Spain, Fax: (+34) 959-219942
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  • Elena Fernández Dr.

    1. Dpt. Química Física i Inorgànica, Universitat Rovira i Virgili, Marcel.lí Domingo s/n, 43007 Tarragona, Spain, Fax: (+34) 977-55-95-63
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Abstract

The complexes [Cu(NHC)(NCMe)]BF4 (NHC=N-heterocyclic ligand), with bis(catecholato)diboron (B2(cat)2) as the boron source, efficiently catalyze the diboration of styrene with very high degrees of conversion. With the appropriate NHC ligand, the reaction proceeds quantitatively toward the diborated derivative PhCH(Bcat)[BOND]CH2(Bcat). The [styrene]/[B2(cat)2] ratio also has a strong effect on the selectivity: the use of an excess of styrene allows modification of the selectivity toward the formation solely of the monoborated derivative, PhCH2[BOND]CH2(Bcat). DFT calculations suggest that no oxidative addition processes take place at copper, but that intermediates containing coordinated σ-bonds are involved in the catalytic cycle.

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