4.6 Article

FeCl2/TBAC efficiently catalyzes domino coupling reactions for constructing indoline-fused tetrahydroisoquinolines

Journal

NEW JOURNAL OF CHEMISTRY
Volume 46, Issue 41, Pages 19643-19647

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2nj04177d

Keywords

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Funding

  1. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
  2. Natural Science Foundation for Colleges and Universities in Jiangsu Province [20KJA530003]
  3. Qinglan Project of Jiangsu Province, Jiangsu Key Laboratory of Biomass Energy [JSBEM202018]
  4. PetroChina Innovation Foundation [2021DQ02-0707]

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FeCl2/TBAC was found to exhibit high catalytic activity for the synthesis of indoline-fused tetrahydroisoquinolines using aryltetrahydroisoquinolines and active methylene as reactants. The reaction proceeded through domino coupling reactions between C-sp3-H and C-sp3-H, and subsequently C-sp3-H and C-sp2-H. EPR spectroscopy revealed the presence of catalytically active species (Fe3+OO center dot) and Fe3+, which enhanced the reaction through HAT and SET processes, respectively.
FeCl2/TBAC has been found to be highly active for the construction of indoline-fused tetrahydroisoquinolines using aryltetrahydroisoquinolines and active methylene as simple reactants. The transformation was proposed to proceed via domino coupling reactions between C-sp3-H and C-sp3-H, and subsequently C-sp3-H and C-sp2-H, respectively. The EPR spectra have been acquired to analyse the catalytically active species, (Fe3+OO center dot) and Fe3+, which accelerated the reaction via HAT and SET processes, respectively.

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