Pd(II)-Catalyzed Intramolecular C(sp<sup>2</sup>)–H Arylation of Tryptamines Using the Nonsteric NH<sub>2</sub> as a Directing Group
Sixi Wang, Bin Yu, Hong‐Min Liu
Abstract
The free amine-directed C–H functionalization reactions are challenging and mainly restricted to bulky amines. In this work, we report the nonsteric NH2-directed Pd(II)-catalyzed intramolecular C(sp2)–H arylation of tryptamines, which enables the efficient, gram-scale, and regioselective synthesis of versatile 2-aryltryptamines (35 examples, up to 98% yield). This approach broadens the substrate scope of the free amine-directed C–H functionalization, not limited to bulky amine substrates. Late-stage elaborations of 2-aryltryptamines achieve the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as aurantioclavine, chimonanthine, and phalarine.
Topics & Concepts
TryptaminesChemistryIntramolecular forceAmine gas treatingRegioselectivitySurface modificationCatalysisYield (engineering)Substrate (aquarium)Functional groupCombinatorial chemistryStereochemistryMedicinal chemistryTryptamineOrganic chemistryPhysical chemistryMaterials sciencePolymerBiochemistryOceanographyMetallurgyGeologyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis