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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Bibliographic Details
Published in:Chemistry : a European journal Vol. 25; no. 48; pp. 11240 - 11245
Main Authors: Zhao, Zhensheng, Ma, Kevin C. Y., Legault, Claude Y., Murphy, Graham K.
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 27.08.2019
Wiley Subscription Services, Inc
Subjects:
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
Online Access:Get full text
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201902818