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Metal-free C–C bond formation via coupling of nitrile imines and boronic acids

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Abstract

The challenges of developing sustainable methods of carbon–carbon bond formation remains a topic of considerable importance in synthetic chemistry. Capitalizing on the highly reactive nature of the nitrile imine 1,3-dipole, we have developed a novel metal-free coupling of this species with aryl boronic acids. Photochemical generation of a nitrile imine intermediate and trapping with a palette of boronic acids enabled rapid and facile access to a broad library of more than 25 hydrazone derivatives in up to 92% yield, forming a carbon–carbon bond in a metal free fashion. This represents the first reported example of direct reaction between boronic acids and a 1,3-dipole.

Graphical abstract: Metal-free C–C bond formation via coupling of nitrile imines and boronic acids

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Publication details

The article was received on 19 Jun 2019, accepted on 16 Sep 2019 and first published on 27 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03032H
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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    Metal-free C–C bond formation via coupling of nitrile imines and boronic acids

    K. Livingstone, S. Bertrand, J. Mowat and C. Jamieson, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03032H

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