4.8 Article

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

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 5, 页码 1381-1385

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711316

关键词

boron; fluorine; nucleophilic substitution; reaction mechanisms; waste prevention

资金

  1. University of Michigan Department of Chemistry
  2. NSF-CAREER program [CHE-1350877]
  3. Direct For Mathematical & Physical Scien [1350877] Funding Source: National Science Foundation
  4. Division Of Chemistry [1350877] Funding Source: National Science Foundation

向作者/读者索取更多资源

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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