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Mechanistic elucidation of HFIP-enabled C-Cl bond activation in the synthesis of tetrahydroquinoline derivatives
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DOI：10.1002/bkcs.70162.png)
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Abstract
En 中文
Hexafluoroisopropanol (HFIP) is a powerful reaction medium that enables transformations involving cationic intermediates, yet the mechanistic basis of its reactivity remains incompletely understood. Herein, we report a mechanistic investigation of the HFIP-mediated transformation of propargylic halides with anilines, affording tetrahydroquinolines through a cascade sequence. Systematic studies reveal that HFIP promotes ionization of propargylic chlorides by stabilizing ion pairs and enhancing effective Br & oslash;nsted acidity. Reaction efficiency is governed by a balance between productive ionization and substrate decomposition, and deuterium-labeling experiments establish that HFIP participates directly in proton transfer during the disproportionation step. These findings provide a unified mechanistic framework for HFIP-enabled C-Cl activation and highlight the potential of highly ionizing solvent systems in bond activation and cascade transformations.
Keywords:
Br & oslash
nsted acidity amplification
C-Cl bond activation
disproportionation
hexafluoroisopropanol (HFIP)
tetrahydroquinolines
Journal
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2.2
Papers:
249
Citations:
4.6K
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