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NHC-Cu-Catalyzed Enantioselective Hydroboration of Acyclic and Exocyclic 1,1-Disubstituted Aryl Alkenes

Authors

  • Dr. Rosa Corberán,

    1. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442
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  • Nicholas W. Mszar,

    1. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442
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  • Prof. Amir H. Hoveyda

    Corresponding author
    1. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442
    • Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442
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  • Financial support was provided by the NSF (CHE-0715138). R.C. is a Spanish Ministry of Science and Innovation postdoctoral fellow. We thank Dr. Y. Lee and H. Jang for helpful discussions and Frontier Scientific for generous gifts of bis(pinacolato)diboron. Mass spectrometry facilities at Boston College are supported by the NSF (CHE-0619576). NHC=N-heterocyclic carbene.

Abstract

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Harte Nuss zu knacken: Chirale zweizähnige NHC-Kupfer-Komplexe wurden entwickelt, die enantioselektive Hydroborierungen einer der problematischsten Substratklassen vermitteln: Acyclische und exocyclische 1,1-disubstituierte Alkene wurden mit >98 % Positionsselektivität in bis zu >98 % Ausbeute und e.r.=96.5:3.5 umgesetzt (siehe Schema, B2(pin)2=Bis(pinakolato)dibor, NHC=N-heterocyclisches Carben).

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