Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
Cecilia Ciccolini, Giacomo Mari, Francesco G. Gatti, Giuseppe Gatti, Gianluca Giorgi, Fabio Mantellini, Gianfranco Favi
Abstract
Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.
Topics & Concepts
IndolineReactivity (psychology)Density functional theorySubstrate (aquarium)CatalysisChemistryCycloadditionCombinatorial chemistryStereochemistryComputational chemistrySubstrate specificityOrganic chemistryEnzymeBiologyAlternative medicinePathologyMedicineEcologyCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesSynthesis and Catalytic Reactions