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B(C6F5)3-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation

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Abstract

Tris(pentafluorophenyl)borane-catalyzed dehydrogenative-cyclization of N-tosylhydrazones with aromatic amines has been disclosed. This metal-free catalytic protocol is compatible with a range of functional groups to provide both symmetrical and unsymmetrical 3,4,5-triaryl-1,2,4-triazoles. Mechanistic experiments and density functional theory (DFT) studies suggest an initial Lewis adduct formation of N-tosylhydrazone with B(C6F5)3 followed by sequential intermolecular amination of the borane adduct with aniline, intramolecular cyclization and frustrated Lewis pair (FLP)-catalyzed dehydrogenation for the generation of substituted 1,2,4-triazoles.

Graphical abstract: B(C6F5)3-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation

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Publication details

The article was received on 22 May 2019, accepted on 05 Jul 2019 and first published on 05 Jul 2019


Article type: Edge Article
DOI: 10.1039/C9SC02492A
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    B(C6F5)3-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation

    M. M. Guru, S. De, S. Dutta, D. Koley and B. Maji, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC02492A

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