Borazine‐CF3− Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation. Issue 5 (9th January 2018)

• Record Type: Journal Article
• Authors: Geri, Jacob B.; Wade Wolfe, Michael M.; Szymczak, Nathaniel K.
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 5(2018)
• Page Start: 1381
• Page End: 1385
• Publication Date: 2018-01-09
• Subjects: boron -- fluorine -- nucleophilic substitution -- reaction mechanisms -- waste prevention; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201711316
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : 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.