铜(I)促进芳香类 C(sp²)—H 键的硝化反应

Nitroaromatic compounds are important chemical raw materials and intermediates, which are widely used in various fields. The development of mild and generally applicable methods for the nitration of arenes has long been a pursuit in organic chemistry. An efficient C(sp²)—H nitration of arenes was developed, using sodium nitrite or tert-butyl nitrite (TBN) as nitrating reagents, 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) as the oxidant in the presence copper(I) catalysts. The nitrated products were obtained in yields up to 96%. This method demonstrates excellent functional group tolerance, accommodating esters, carbonyls, nitro, cyano, and halogen groups. Furthermore, it exhibits broad substrate scope, encompassing electron-rich and electron-deficient arenes, as well as complex pharmaceutical molecules.