Borazine‐CF3− Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation

A fluoroform‐derived borazine CF3− transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-01, Vol.57 (5), p.1381-1385
Main Authors: Geri, Jacob B., Wade Wolfe, Michael M., Szymczak, Nathaniel K.
Format: Article
Language:English
Subjects:
Additives
Adducts
Aromatic compounds
boron
Catalysis
fluorine
nucleophilic substitution
Organic chemistry
Periodic table
reaction mechanisms
Room temperature
Transition metals
Trifluoromethane
waste prevention
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Summary:A fluoroform‐derived borazine CF3− transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C−H and C−X trifluoromethylation reactions. Mechanistic analysis supports a dissociative mechanism for CF3− transfer, and cation modification afforded a reagent with enhanced stability. A trifluoromethylating matter: A stable fluoroform‐derived reagent facilitates the nucleophilic trifluoromethylation of a broad array of inorganic and organic electrophiles (E) at room temperature. The reaction scope includes 18 inorganic elements, nucleophilic aromatic substitution, and CF3− addition to carbonyl and imine compounds. Kinetic analysis supports a dissociative mechanism.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201711316