Organocatalyst That Activates Nitro Groups for Coupling Reactions
Anti-1,2,2,3,4,4-hexamethylphosphetane 1-oxide (H1766) is a TCI organocatalyst that activates nitro groups for coupling reactions. It reacts with amino groups to form N-N bonds, giving the corresponding hydrazine derivatives in good yields.¹⁾ ²⁾ H1766 also catalyzes the deoxygenative C-N cross-coupling of nitro(hetero)arenes with (hetero)arylboronic acids, enabling the synthesis of di(hetero)arylamines.²⁾ In the reaction schemes, the reagents used are Diphenylsilane (D2820), Phenylsilane (P1291) and 2,4,6-trimethylbenzoic acid (T1421).¹⁾ ²⁾ As a practical example, a secondary arylamine was synthesized from 1-bromo-2-nitrobenzene and phenylboronic acid using H1766 (0.15 equiv.) and Phenylsilane in refluxing CPME for 4 h, giving a yield of 89.3%.²⁾
Related products
- TCI H1766 33530-51-7 anti-1,2,2,3,4,4-Hexamethylphosphetane 1-Oxide
- TCI T1421 480-63-7 2,4,6-Trimethylbenzoic Acid
References
- PIII/PV═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. doi:10.1021/jacs.1c07272
- An Improved PIII/PV═O-Catalyzed Reductive C–N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product-Determining Steps. G. Li, T. V. Nykaza, J. C. Cooper, A. Ramirez, M. R. Luzung, A. T. Radosevich, J. Am. Chem. Soc. 2020, 142, 6786. doi:10.1021/jacs.0c01666
Download TCI brochure Organocatalyst for Coupling Reactions by Activation of Nitro Group (PDF)
Source
- TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20210621
- TCI product page H1766: tcichemicals.com/ID/en/p/H1766
- TCI brochure RR160: Organocatalyst for Coupling Reactions by Activation of Nitro Group
For research and laboratory use only, not for human consumption.
