Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 17, Issue 14, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202200190
Keywords
Sulfoxide; Friedel-Crafts alkylation; Trifluoroethyl; Thionium; Pummerer reaction
Categories
Funding
- Chinese Academy of Science
- National Natural Science Foundation of China [21032006, 21672138]
- 973 Program of China [2012CBA01200]
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In this study, the classical Pummerer rearrangement efficiently produced S,O-acetal under specific conditions, and regenerated the reactive intermediate through the co-solvent, enabling the synthesis of 1-thiyl-2,2,2-trifluoroethyl arenes with excellent yields under metal-free conditions.
The classical Pummerer rearrangement of 2,2,2-trifluoroethylaryl sulfoxide with trifluoracetic anhydride (TFAA) affords the S,O-acetal efficiently. In the presence of trifluoracetic acid (TFA) as the co-solvent, the S,O-acetal can regenerate reactive thionium intermediate of Pummerer rearrangement. When employing arenes as nucleophiles, this strategy produces corresponding 1-thiyl-2,2,2-trifluoroethyl arenes with excellent yields under metal-free conditions.
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