Solvent-Free, Microwave-Assisted N-Arylation of Indolines by using Low Palladium Catalyst Loadings

Authors

  • Dr. Luca Basolo,

    1. DISMAB, Sezione di Chimica Organica “A. Marchesini”, Università degli Studi di Milano via Venezian 21,20133 Milano (Italy), Fax: +39-02-50314476
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  • Alice Bernasconi,

    1. DISMAB, Sezione di Chimica Organica “A. Marchesini”, Università degli Studi di Milano via Venezian 21,20133 Milano (Italy), Fax: +39-02-50314476
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  • Dr. Elena Borsini,

    1. DISMAB, Sezione di Chimica Organica “A. Marchesini”, Università degli Studi di Milano via Venezian 21,20133 Milano (Italy), Fax: +39-02-50314476
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  • Prof. Dr. Gianluigi Broggini,

    1. Dipartimento di Scienze Chimiche e Ambientali, Università dell'Insubria via Valleggio 11, 22100 Como (Italy)
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  • Prof. Dr. Egle M. Beccalli

    Corresponding author
    1. DISMAB, Sezione di Chimica Organica “A. Marchesini”, Università degli Studi di Milano via Venezian 21,20133 Milano (Italy), Fax: +39-02-50314476
    • DISMAB, Sezione di Chimica Organica “A. Marchesini”, Università degli Studi di Milano via Venezian 21,20133 Milano (Italy), Fax: +39-02-50314476
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Abstract

Indoline-based compounds are abundant in nature, and the indoline skeleton is an often-encountered scaffold in a range of biologically active alkaloids, pharmaceutically active compounds, and functional molecules (e.g., sensitizers for solar cells). The wide range of uses warrants further interest in the structural modification of this class of compounds. A series of substituted N-aryl indolines is prepared by a solvent-free, palladium-catalyzed procedure. The procedure requires only low loadings of catalyst, uses microwave irradiation, and starts from commercially available substrates. The method proceeds in good yields and in short reaction times with aryl bromides, chlorides, and iodides, also on 2-substituted indolines. The combination of solvent-free methods with microwave heating will further increase in importance in the search for more environmentally acceptable synthesis methods.

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