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

Livingstone, Keith and Betrand, Sophie and Mowat, Jenna and Jamieson, Craig (2019) Metal free C-C bond formation via coupling of nitrile imines and boronic acids. Chemical Science, 10 (44). pp. 10412-10416. ISSN 2041-6520

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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.