Synthesis of pyrrole derivatives via ordered isocyanide insertion reaction driven by ring strain mediated by non-covalent bond interactions†

An efficient synthesis of pyrrole derivatives is achieved via ordered isocyanide insertion reaction, driven by ring strain and mediated by intramolecular non-covalent bonds. This method harnesses the strategic design of precursors to control reactivity, ensuring selectivity and high yields. The strategy is noteworthy for its innovative utilization of α,β-unsaturated ketone, which concurrently serves as both a directing group and an integral reaction substrate. Additionally, we have demonstrated the sequential de-tert-butylation of the same substrate under alkaline or acidic conditions. The plausible mechanism has been further corroborated through DFT theoretical calculations, providing a solid foundation for our proposed route.