Chameleon boron switches between electrophile and nucleophile

Chameleon

Source: © Daniel Hernanz Ramos/Getty Images

Mida boronates can be either electrophilic or nucleophilic in rearrangement reactions

A class of nitrogen-stabilised boron compounds can switch between their established electrophilic and unprecedented nucleophilic behaviour, researchers have revealed. Tapping into this unusual reactivity, the Canadian team behind the study discovered several boryl shift reactions that are analogues of well-known carbon transformations like the pinacol rearrangement.