C(sp2)–H Bond Multiple Functionalization in Air for Construction of Tetrahydrocarbazoles with Continuous Quaternary Carbons and Polycyclic Diversification
Longlong Song, Dan Ni, Shi‐Kun Jia, Rou Pi, Suzhen Dong, Fan Yang, Jie Tang, Shunying Liu
Abstract
)-H function of indole ketone with diazo compound via a rhodium(II)-catalyzed intramolecular electrophilic trapping reaction under mild conditions in air was demonstrated. The established methodology provided a highly efficient approach for direct synthesis of mutisubstituted tetrahydrocarbazoles with continuous quaternary carbons. The resulting products facilitate further modification to conveniently construct tetrahydrocarbazoles with additional fused heterocyclic rings. By phenotypic screening, several products exhibit good anticancer bioctivities in osteosarcoma cell lines.
Topics & Concepts
ChemistryIntramolecular forceElectrophileIndole testCombinatorial chemistryKetoneRhodiumSurface modificationDiazoCatalysisStereochemistryOrganic chemistryPhysical chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions