External Reductant-Free Palladium-Catalyzed Reductive Insertion of Isocyanide: Synthesis of Polysubstituted Pyrroles and Its Applications as a Cysteine Probe

• DOI: 10.1021/acs.orglett.9b01220
• Publication Date: 2019-05-10T12:04:55Z
• Authors: Dianpeng Chen; Yingying Shan; Jianming Li; Jinmao You; Xuejun Sun; Guanyinsheng Qiu
• Keywords: Synthon; Reductive elimination; Cyanation; Migratory insertion

In this work, an unprecedented route is described for the synthesis of 2-amino-4-cyanopyrrole derivatives via palladium-catalyzed reductive isocyanide insertion alkynyl imines. reactions, no external reductant added and plays a dual role as both C1 synthon imidoylation cyano source cyanation. Mechanism studies suggest [4 + 1] cycloaddition, insertion, β-carbon elimination, palladium hydride-based reduction are involved. Moreover, application 2-amine-4-cyanopyrroles cysteine probe realized to detect cysteine.