Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 5, Pages 1381-1385Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711316
Keywords
boron; fluorine; nucleophilic substitution; reaction mechanisms; waste prevention
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Funding
- University of Michigan Department of Chemistry
- NSF-CAREER program [CHE-1350877]
- Direct For Mathematical & Physical Scien [1350877] Funding Source: National Science Foundation
- Division Of Chemistry [1350877] Funding Source: National Science Foundation
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A fluoroform-derived borazine CF3- transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 degrees 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.
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