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Updated: Dec 27, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Metal-free C-C bond formation via coupling of nitrile imines and boronic acids
Keith Livingstone1, Sophie Bertrand2, Jenna Mowat1
1Department of Pure and Applied Chemistry , University of Strathclyde , 295 Cathedral St , Glasgow G1 1XL , UK .
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.
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