The Heck reaction of allylic alcohols catalysed by an N-heterocyclic carbene-Pd(ii) complex and toxicity of the ligand precursor for the marine benthic copepod Amphiascoides atopus

The palladium-catalysed reaction of aryl halides and allylic alcohols is an attractive method for obtaining alpha,beta-unsaturated aldehydes and ketones, which represent key intermediates in organic synthesis. In this context, a 1,2,3-triazol-5-ylidene (aNHC)-based palladium(ii) complex formed in situ has been found to be a selective catalyst for the syntheses of building blocks from the corresponding aryl halides and allylic alcohols, with yields ranging from 50% to 90%. The lack of toxic effects of the ligand precursor (1,2,3-triazolium salt) of the palladium(ii) complex for the harpacticoid copepod Amphiascoides atopus allowed us to contrast the efficiency of the catalytic system with the potential impact of the principal waste chemical in global aquatic ecosystems, which has not been previously addressed.

Automated summary

The palladium-catalysed reaction of aryl halides and allylic alcohols is an important method for obtaining alpha, beta-unsaturated aldehydes and ketones. A 1,2,3-triazol-5-ylidene (aNHC)-based palladium(ii) complex formed in situ has been found to be a selective catalyst with yields ranging from 50% to 90%. The lack of toxic effects of the ligand precursor on the harpacticoid copepod Amphiascoides atopus allows for a comparison of catalytic efficiency with the potential impact of waste chemicals on global aquatic ecosystems.