6533b7d6fe1ef96bd126671c
RESEARCH PRODUCT
Electrochemical nitration with nitrite
Siegfried R. WaldvogelLukas SchäfferStephan P. BlumTarik KarakayaChristean Nickelsubject
Green chemistryReaction mechanism540 Chemistry and allied sciencesSupporting electrolyteGeneral Chemical EngineeringElectrochemistryCombinatorial chemistrySolventchemistry.chemical_compoundGeneral EnergychemistryNitrationYield (chemistry)540 ChemieEnvironmental ChemistryGeneral Materials ScienceNitritedescription
Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4 NO2 , 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-10-22 |