When chirality breaks: mechanochemical degradation of biaryl atropisomers

Abstract

We investigated the stereochemical stability of biaryl atropisomers under conditions typically employed in organic mechanosynthesis. Systematic variation of reaction parameters revealed three degradation pathways: racemisation, cyclisation, and oligomerisation. This previously overlooked behaviour critically impacts catalytic performance in asymmetric synthesis, highlighting the need for rigorous stability assessment during mechanochemical reactions.