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Phenalenyl-based ligand for transition metal chemistry: Application in Henry reaction

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Abstract

We report the synthesis and characterization of the first transition metal complex of a phenalenyl-based ligand. The reaction of Cu(OAc)2.H2O with 9-N-methylamino-1-N ′-methylimino-phenalene (LH) in 1:1 stoichiometric ratio results in the formation of a mononuclear copper complex [LCu(OAc)] (1). The molecular structure of 1 was established by X-ray crystallography. The electrochemistry of 1 indicates the formation of an anionic radical by one electron reduction into the non-bonding molecular orbital of the phenalenyl system. The complex 1 efficiently catalyses the C–C bond forming Henry reaction.

We report the synthesis and characterization of the first transition metal complex of a phenalenyl-based ligand. The electrochemistry of the copper phenalenyl complex reveals the formation of an anionic radical by one electron reduction. The copper phenalenyl complex efficiently catalyses Henry reaction with very high isolated yield at mild reaction conditions.

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Authors and Affiliations

  1. Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER)-Kolkata, Mohanpur, 741252, India

    ARUP MUKHERJEE, TAMAL K SEN & SWADHIN K MANDAL

  2. Georg-August-Universität Göttingen, Tammannstr. 4, 37077, Göttingen, Germany

    DANIEL KRATZERT, DIETMAR STALKE & ALEXANDER DÖRING

  3. School of Chemistry, Trinity College Dublin, Dublin 2, Ireland

    CAROLA SCHULZKE

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  1. ARUP MUKHERJEE
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  2. TAMAL K SEN
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  3. SWADHIN K MANDAL
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  4. DANIEL KRATZERT
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  5. DIETMAR STALKE
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  6. ALEXANDER DÖRING
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  7. CAROLA SCHULZKE
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Correspondence to SWADHIN K MANDAL.

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MUKHERJEE, A., SEN, T.K., MANDAL, S.K. et al. Phenalenyl-based ligand for transition metal chemistry: Application in Henry reaction. J Chem Sci 123, 139–144 (2011). https://doi.org/10.1007/s12039-011-0107-2

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