Palladium-catalysed reductive carbonylation of aryl halides

Fludioxonil is a synthetic fungicide compound of the phenylpyrrole group of substances. It can be used to control fungal disease, making it a useful seed treatment as well as a post-harvest treatment for fruit. Fludioxonil is a broad-spectrum fungicide which is non-systemic with a long residual activity.

The mode of action of fludioxonil is the inhibition of transport-associated phosphorylation of glucose as well as preventing glycerol synthesis. This fungicide is allowed for use in US/Europe (except Austria) and Asia and, so far, was mainly produced by Syngenta (Novartis) at the 106 tons/year scale.

Starting next year, one of the major generic agrochemical companies Adama Israel (former Makhteshim-Agam) is planning to initiate manufacturing of this product using local and international facilities.

The task of our group is to design a novel synthetic strategy toward the synthesis of a key intermediate toward Fludioxonil using more efficient and catalytic methods. We report now the de novo designed synthetic approach to the desired target molecule.