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

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.

SUBMITTER: Livingstone K

PROVIDER: S-EPMC6988605 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Metal-free C-C bond formation <i>via</i> coupling of nitrile imines and boronic acids.

Livingstone Keith K Bertrand Sophie S Mowat Jenna J Jamieson Craig C

Chemical science 20190927 44

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 derivative ...[more]

PMID: 32110332

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