Microwave Radiation for Organolithium Chemistry: Mechanistic Studies on the Direct α-Metalation of a Tertiary Amine.

ABSTRACT: Deprotonation reactions with lithium alkyls exhibit a high temperature dependency. However, the reactivity of lithium alkyls with conventionally used Lewis bases limits their deprotonation capability of more challenging substrates like tertiary amines. Therefore, we have focused on the use of high but exactly set reaction temperatures by usage of microwave radiation in the deprotonation reaction of a tertiary amine in the absence of polar additives. Our study proves the robustness of lithium alkyls, like t-butyllithium and α-metalated tertiary amines under microwave conditions. A solid-state structure of the prelithiation aggregate and quantum chemical calculations offer an insight into the mechanism, revealing that the substrate amine performs as Lewis base for deaggregation itself. By ou

SUBMITTER: Schmidt A 

PROVIDER: S-EPMC12462239 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature