TFA‐Promoted Intermolecular Friedel‐Crafts Alkylation of Arenes with 2,2,2‐Trifluoroethylaryl Sulfoxides

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....

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Published in:Chemistry, an Asian journal an Asian journal, 2022-07, Vol.17 (14), p.e202200190-n/a
Main Authors: Deng, Zhen, Qiu, Liu‐Yan, Pan, Wenjie, Qian, Baiyu, Chen, Jie, Zhang, Hui, Chen, Qing‐Yun, Cao, Weiguo, Tang, Xiao‐Jun
Format: Article
Language:English
Subjects:
Alkylation
Aromatic compounds
Chemistry
Friedel-Crafts alkylation
Nucleophiles
Pummerer reaction
Sulfoxide
Sulfoxides
Thionium
Trifluoroethyl
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Summary: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. α‐CF3 thionium is a reactive intermediate of Pummerer rearrangement of corresponding 2,2,2‐trifluoroethylaryl sulfoxide. When using TFA.as the solvent at elevated temperature, this analogue of trifluoroethyl carbocation can be restored from S,O‐acetal to achieve Friedel‐Crafts alkylation of arenes.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.202200190