期刊
CHEMSUSCHEM
卷 14, 期 22, 页码 4936-4940出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202102053
关键词
electrochemistry; green chemistry; nitrogen oxides; radicals; synthetic methods
资金
- Deutsche Forschungsgemeinschaft [DFG: Wa1276/17-2]
- Merck Sharp Dohme
- Projekt DEAL
This study demonstrates the electrochemical aromatic nitration using NBu4NO2 as the nitro source, with 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increasing the yield by solvent control. The reaction is scalable and shows yields of up to 88%.
Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4NO2, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO2, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up.
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