Carbocations are highly electrophilic intermediates involved in SN1 reactions, such as the direct alkylation of low-reactivity nucleophiles, however, in situ activation of leaving groups in such reactions remains challenging due to the unstable nature of the carbocations, leading to cross-reactivity between nucleophiles and leaving group activators. Here, the authors develop a two-step procedure to avoid such cross-reactivity: they generate carbocationoids as coordinatively stabilized carbocations in one nucleophile-free solution, and then complete the alkylation in another reaction vessel under mild conditions.
- Hikaru Fujita
- Daichi Shimada
- Munetaka Kunishima