Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2‐Trifluoroethyl)arenes

Reacting hydrazones of arylaldehydes with Togni's CF 3 ‐benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2‐trifluoroethyl)arenes. This novel reaction was tolerant to many electronically‐...

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Vydáno v:Chemistry : a European journal Ročník 25; číslo 48; s. 11240 - 11245
Hlavní autoři: Zhao, Zhensheng, Ma, Kevin C. Y., Legault, Claude Y., Murphy, Graham K.
Médium: Journal Article
Jazyk:angličtina
Vydáno: WEINHEIM Wiley 27.08.2019
Wiley Subscription Services, Inc
Témata:
Aromatic compounds
Benzaldehyde
Cesium
Cesium fluorides
Chemistry
Chemistry, Multidisciplinary
Functional groups
Hydrazones
Physical Sciences
Potassium hydroxide
Potassium hydroxides
Reagents
Science & Technology
Substitution reactions
Substrates
Transition metals
hypervalent iodine
NUCLEOPHILIC TRIFLUOROMETHYLATION
C-H TRIFLUOROETHYLATION
MOLECULAR CALCULATIONS
Wolff-Kishner
ARYLBORONIC ACIDS
CROSS-COUPLING REACTIONS
COPPER-CATALYZED TRIFLUOROMETHYLATION
METAL-FREE TRIFLUOROMETHYLATION
trifluoromethylation
ORGANIC HALIDES
ARYL IODIDES
BASIS-SETS
hydrazones
fluorine
ISSN:0947-6539, 1521-3765
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Popis
Shrnutí:Reacting hydrazones of arylaldehydes with Togni's CF 3 ‐benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2‐trifluoroethyl)arenes. This novel reaction was tolerant to many electronically‐diverse functional groups and substitution patterns, as well as naphthyl‐ and heteroaryl‐derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal‐free.
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content type line 14
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201902818