Cu-Catalyzed [1,3]-Fluorine Rearrangement Reactions of N-Fluoroanilines

Area of Science:

• Organic Chemistry
• Catalysis
• Fluorine Chemistry

Background:

• N-fluoro-N-sulfonylanilines are precursors for fluorinated compounds.
• Site-selective C-F bond formation is crucial in organic synthesis.
• Copper catalysis offers versatile reaction pathways.

Purpose of the Study:

• To investigate copper-catalyzed reactions of N-fluoro-N-sulfonylanilines.
• To achieve site-selective fluorine atom rearrangement.
• To synthesize 2-fluorosulfonanilides.

Main Methods:

• Copper-catalyzed reaction of N-fluoro-N-sulfonylanilines.
• Analysis of reaction products.
• Density Functional Theory (DFT) calculations to elucidate the mechanism.

Main Results:

• Successful synthesis of 2-fluorosulfonanilides in good to acceptable yields.
• Demonstration of a [1,3]-fluorine rearrangement from nitrogen to the ortho-carbon.
• DFT calculations support a mechanism involving Cu(III) coordination and C-F bond formation.

Conclusions:

• Copper catalysis facilitates a novel site-selective [1,3]-fluorine rearrangement.
• The reaction provides an efficient route to ortho-fluorinated sulfonamides.
• The proposed mechanism offers insights into copper-mediated C-F bond formation.