Synthesis of 2-substituted indolines using sequential Pd-catalyzed processesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for all products without elemental analysis data (3c–g and 4d–g). See http://www.rsc.org/suppdata/p1/b2/b200163b/

Indole and indoline derivatives were selectively and temperature dependently synthesized via the intramolecular cross‐coupling reaction between the amino and aromatic bromine functionalities of 2‐bromophenethylamine derivatives in the presence of 10% palladium on carbon (Pd/C), 1,1′‐bis(diphenylphosphino)ferrocene (DPPF), and sodium tert‐butoxide (NaO‐t‐Bu) in mesitylene at 140 and 200 °C, respectively. The neutralization using acetic acid after formation of the indoline derivatives effectively promoted their aromatization, and the corresponding indole derivatives were obtained at 140 °C. Furthermore, various aryl groups were also introduced to the N‐1 position of the indole, pyrrole, and carbazole rings by their direct intramolecular arylation with aryl halides and a one‐pot protocol for N‐arylindole synthesis from 2‐bromophenethylamine was developed.magnified image

show abstract

Construction of Optically Active Indolines by Formal [4+1] Annulation of Sulfur Ylides and N‐(ortho‐Chloromethyl)aryl Amides

Yang

Wang

et al. 2013

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Synthesis of 2-substituted indolines using sequential Pd-catalyzed processesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for all products without elemental analysis data (3c–g and 4d–g). See http://www.rsc.org/suppdata/p1/b2/b200163b/

Cited by 24 publications

References 18 publications

Synthesis of Saturated Five‐Membered Nitrogen Heterocycles via Pd‐Catalyzed CN Bond‐Forming Reactions

Synthesis of Saturated Five‐Membered Nitrogen Heterocycles via Pd‐Catalyzed CN Bond‐Forming Reactions

Palladium on Carbon‐Catalyzed One‐Pot N‐Arylindole Synthesis: Intramolecular Aromatic Amination, Aromatization, and Intermolecular Aromatic Amination

Construction of Optically Active Indolines by Formal [4+1] Annulation of Sulfur Ylides and N‐(ortho‐Chloromethyl)aryl Amides

Contact Info

Product

Resources

About