Organocatalyst for Hydrazine Derivative Synthesis by Cross-Coupling of Nitroarenes and Anilines

anti-1,2,2,3,4,4-Hexamethylphosphetane 1-oxide (1) is a catalyst for cross-coupling of nitroarenes and anilines to afford corresponding hydrazine derivatives in good yield.¹⁾ 1 enables activating nitro compounds via P^III/P^V redox cycling. The activated nitroarenes react with amines to form N-N bonds and give the corresponding hydrazine. Furthermore, 1 catalyses the reductive C-N coupling with aryl boronic acids.²⁾ Further developments in this chemistry are ongoing, potentially leading to new industrial processes.

Related Products

H1766

anti-1,2,2,3,4,4-Hexamethylphosphetane 1-Oxide

D2820

Diphenylsilane

T1421

2,4,6-Trimethylbenzoic Acid

References

• 1) P^III/P^V=O-Catalyzed Intermolecular N-N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines
  • G. Li, S. P. Miller, A. T. Radosevich, J. Am. Chem. Soc. 2021, 143, 14464.
• 2) An Improved P^III/P^V=O-Catalyzed Reductive C-N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product- Determing Steps
  • G. Li, T. V. Nykaza, J. C. Cooper, A. Ramirez, M. R. Luzung, A. T. Radosevich, J. Am. Chem. Soc. 2020, 142, 6786.

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