Double C[BOND]H Activation of an N-Heterocyclic Carbene Ligand in a Ruthenium Olefin Metathesis Catalyst

Authors

  • Soon Hyeok Hong,

    1. The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA, Fax: (+1) 626-564-9297
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  • Anatoly Chlenov,

    1. The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA, Fax: (+1) 626-564-9297
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  • Michael W. Day Dr.,

    1. Beckman Institute, X-ray Crystallography Laboratory, California Institute of Technology, Pasadena, CA 91125, USA
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  • Robert H. Grubbs Prof.

    1. The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA, Fax: (+1) 626-564-9297
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  • The authors thank Lawrence M. Henling for his contributions to the X-ray crystallography determinations, and Dr. Mona Shahgholi for performing the mass spectrometric analyses. This research is supported by the National Science Foundation.

Abstract

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Having a breakdown: Decomposition of the olefin metathesis catalyst [(biph)(PCy3)Cl2Ru[DOUBLE BOND]C(H)Ph] (biph= N,N′-diphenylbenzimidazol-2-ylidene, Cy=cyclohexyl) results in benzylidene insertion into an ortho C[BOND]H bond of an N-phenyl group of the biph ligand. The ruthenium center further inserts into another ortho C[BOND]H bond of the other N-phenyl ring to give a new Ru[BOND]C bond as a part of a five-membered metallacycle (see scheme).

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