B(CF)-catalyzed dehydrogenative cyclization of -tosylhydrazones and anilines a Lewis adduct: a combined experimental and computational investigation.

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2019
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Abstract
Tris(pentafluorophenyl)borane-catalyzed dehydrogenative-cyclization of -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 -tosylhydrazone with B(CF) 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.
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Authors Guru, Murali Mohan;De, Sriman;Dutta, Sayan;Koley, Debasis;Maji, Biplab;
Journal Chemical science
Year 2019
DOI
10.1039/c9sc02492a
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Keywords
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