4055-70-3

Upstream product

• 32905-00-3 4-Nitropyrogallol-1,2-dibenzolsulfonat-3-methylether 
• 93655-97-1 Pyrogallol-1.2-dibenzolsulfonat 
• 33025-82-0 4-Nitropyrogallol-1,2-dibenzolsulfonat 
• 67-56-1 methanol 
• 91458-98-9 4-nitrocyclohexa-3,5-diene-1,2-dione 
• 100-02-7 4-nitro-phenol 
• 554-84-7 meta-nitrophenol 
• 619-08-9 2-chloro-4-nitrophenol 

Relevant academic research and scientific papers

Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents

Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.