A novel copper-mediated chelation-assisted ortho C-H nitration of (hetero)arenes has been developed for the first time, which used dioxygen as terminal oxidant and 1,2,3-TCP as solvent, leading to the synthesis of nitroaromatics with excellent regioselectivity and in good yields. Mechanistic investigations indicate a mechanism involving a four-centered transition state, with simultaneous cleavage of an ortho C-H bond and a N-O bond of the nitrate anion on the 2-arylpyridine-coordinated copper(II) complex.
A novel copper-mediated chelation-assisted ortho C-H nitration of (hetero)n class="Chemical">arenes has been developed for the first time, which used dioxygen as terminal oxidant and 1,2,3-TCP as solvent, leading to the synthesis of nitroaromatics with excellent regioselectivity and in good yields. Mechanistic investigations indicate a mechanism involving a four-centered transition state, with simultaneous cleavage of an ortho C-H bond and a N-O bond of the nitrate anion on the 2-arylpyridine-coordinated copper(II) complex.
Authors: Junghyea Moon; Hyun Ku Ji; Nayoung Ko; Harin Oh; Min Seo Park; Suho Kim; Prithwish Ghosh; Neeraj Kumar Mishra; In Su Kim Journal: Arch Pharm Res Date: 2021-10-18 Impact factor: 4.946