Litcius/Paper detail

Divergent C–H activation synthesis of chalcones, quinolones and indoles

Yuesen Shi, Huimin Xing, Tianle Huang, Xuexin Liu, Jian Chen, Xiao-Yu Guo, Guo‐Bo Li, Yong Wu

2020Chemical Communications54 citationsDOI

Abstract

We here report a condition-controlled divergent synthesis strategy of chalcones, quinolones and indoles, which was achieved via a C-H activation reaction of N-nitrosoanilines and cyclopropenones. Variations of Ag salts are observed to be crucial for divergently constructing the three distinct chemical scaffolds. A Rh(i)- and Rh(iii)-cocatalyzed decarbonylation/C-H activation/[3+2] annulation cascade reaction was developed for the synthesis of indoles. These methodologies are characterized by mild reaction conditions, high functional group tolerance, and amenability to gram-scale synthesis, providing a reference for future derivation of new chemical scaffolds by C-H activation.

Topics & Concepts

AnnulationChemistryDecarbonylationCombinatorial chemistryReaction conditionsChemical synthesisStereochemistryCatalysisOrganic chemistryBiochemistryIn vitroCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions