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Visible-light induced copper(I)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes

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Abstract

Visible light mediated copper catalysed denitrogenative oxidative coupling of 2-hydrazinopyridines with terminal alkynes to form 2-(alkyl/arylethynyl) pyridines in the presence of O2 at room temperature is reported with 42 examples. This is the first report on visible light stimulated N2 elimination by an in situ generated copper(II) superoxo/peroxo complex. N2 and water are the only by-products. The green chemistry metrics evaluation signifies that the current method is ecofriendly and economically feasible. This method allows the green synthesis of mGluR5 receptor antagonists, 2-methyl-6-(phenylethynyl)pyridine (MPEP) and 2-((3-methoxyphenyl)ethynyl)-6-methylpyridine (M-MPEP).

Graphical abstract: Visible-light induced copper(i)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes

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Publication details

The article was received on 14 Apr 2018, accepted on 02 Aug 2018 and first published on 02 Aug 2018


Article type: Communication
DOI: 10.1039/C8GC01180J
Citation: Green Chem., 2018, Advance Article
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    Visible-light induced copper(I)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes

    V. P. Charpe, A. A. Hande, A. Sagadevan and K. C. Hwang, Green Chem., 2018, Advance Article , DOI: 10.1039/C8GC01180J

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