Recent Advances and Uses of (Me4N)XCF3 (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

The introduction of trifluoromethylthio (SCF3) and trifluoromethylseleno (SeCF3) substituents into organic molecules significantly improves the electron‐withdrawing and lipophilic properties of their parent compounds. Therefore, a vast class of versatile reagents were employed to access the correspo...

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Veröffentlicht in:Asian journal of organic chemistry 2021-01, Vol.10 (1), p.61-73
Hauptverfasser: Yang, Xi‐Hui, Chang, Denghu, Zhao, Rong, Shi, Lei
Format: Artikel
Sprache:eng
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Zusammenfassung:The introduction of trifluoromethylthio (SCF3) and trifluoromethylseleno (SeCF3) substituents into organic molecules significantly improves the electron‐withdrawing and lipophilic properties of their parent compounds. Therefore, a vast class of versatile reagents were employed to access the corresponding fluorine‐containing compounds. Among them, tetramethylammonium salts, such as (Me4N)SCF3 and (Me4N)SeCF3, have been employed as practical and efficient non‐metal reagents for developing efficient trifluoromethylthiolation and trifluoromethylselenolation in recent years. This Minireview systematically illustrates the application of (Me4N)XCF3 (X=S, Se) in the synthesis of trifluoromethylthiolated and trifluoromethylselenolated compounds, and its content is divided into two categories: transition‐metal‐catalyzed reactions, and transition‐metal‐free reactions. The tetraalkylammonium salts (Me4N)SCF3 and (Me4N)SeCF3 have recently enabled the direct introduction of trifluoromethylthio (SCF3) and trifluoromethylseleno (SeCF3) substituents into a range of organic molecules. This Minireview systematically illustrated this efficient functionalization, and the examples were surveyed and organized into the following two categories: transition‐metal‐catalyzed reactions, and transition‐metal‐free reactions.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202000575