152376-94-8

Basic information

• Product Name: ⁿBu₄N⁺[Cu(CF₃)₄]^-
• CAS NO: 152376-94-8
• Molecular Weight: 582.039
• Mol File: 152376-94-8.mol

Chemical Properties

• CAS DataBase Reference: ⁿBu₄N⁺[Cu(CF₃)₄]^-(CAS DataBase Reference)
• NIST Chemistry Reference: ⁿBu₄N⁺[Cu(CF₃)₄]^-(152376-94-8)
• EPA Substance Registry System: ⁿBu₄N⁺[Cu(CF₃)₄]^-(152376-94-8)

Safety Data

• Hazardous Substances Data: 152376-94-8(Hazardous Substances Data)

Usage

Uses

ⁿBu₄N⁺[Cu(CF₃)₄]^- is used as a reagent in the field of organic chemistry for various applications, including:
1. Carbon-Carbon Bond-Forming Reactions:
ⁿBu₄N⁺[Cu(CF₃)₄]^- is used as a catalyst for carbon-carbon bond-forming reactions due to its ability to facilitate the formation of new carbon-carbon bonds, which are crucial in the synthesis of complex organic molecules.
2. Cross-Coupling Reactions:
In the context of cross-coupling reactions, ⁿBu₄N⁺[Cu(CF₃)₄]^- is used as a catalyst to promote the coupling of different organic fragments, leading to the formation of more complex molecular structures.
3. Palladium-Catalyzed Reactions:
ⁿBu₄N⁺[Cu(CF₃)₄]^- is used as a source of copper in palladium-catalyzed reactions, where it aids in enhancing the efficiency and selectivity of the catalytic process.
4. Organic Synthesis:
ⁿBu₄N⁺[Cu(CF₃)₄]^- is used as a reagent in organic synthesis for its ability to participate in a variety of reactions, making it a versatile tool for the construction of diverse organic compounds.

Upstream product

• 1643-19-2 tetrabutylammomium bromide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 

Relevant articles and documents

C(sp3)-CF3Reductive Elimination from a Five-Coordinate Neutral Copper(III) Complex

The reductive elimination from a high-valent late-transition-metal complex for the formation of a carbon-carbon or carbon-heteroatom bond represents a fundamental product-forming step in a number of catalytic processes. While reductive eliminations from well-defined Pt(IV), Pd(IV), Ni(III)/Ni(IV), and Au(III) complexes have been studied, the analogous reactions from neutral Cu(III) complexes remain largely unexplored. Herein, we report the isolation of a stable, five-coordinate, neutral square pyramidal Cu(III) complex that gives CH3-CF3 in quantitative yield via reductive elimination. Mechanistic studies suggest that the reaction occurs through a synchronous bond-breaking/bond-forming process via a three-membered ring transition state.

A Key Intermediate in Copper-Mediated Arene Trifluoromethylation, [nBu4N][Cu(Ar)(CF3)3]: Synthesis, Characterization, and C(sp2)?CF3 Reductive Elimination

The synthesis, characterization, and C(sp2)?CF3 reductive elimination of stable aryl[tris(trifluoromethyl)]cuprate(III) complexes [nBu4N][Cu(Ar)(CF3)3] are described. Mechanistic investigations, including kinetic studies, studies of the effect of temperature, solvent, and the para substituent of the aryl group, as well as DFT calculations, suggest that the C(sp2)?CF3 reductive elimination proceeds through a concerted carbon–carbon bond-forming pathway.

Copper-Mediated Trifluoromethylation of Benzylic Csp3?H Bonds

Trifluoromethyl-containing compounds play a significant role in medicinal chemistry, materials and fine chemistry. Although direct C?H trifluoromethylation has been achieved on Csp2?H bonds, direct conversion of Csp3?H bonds to Csp3?CF3 remains challenging. We report herein an efficient protocol for the selective trifluoromethylation of benzylic C?H bonds. This process is mediated by a combination CuIII?CF3 species and persulfate salts. A wide range of methylarenes can be selectively trifluoromethylated at the benzylic positions. A combination of experimental and theoretical mechanistic studies suggests that the reaction involves a radical intermediate and a CuIII?CF3 species as the CF3 transfer reagent.