Highly selective C3–H iodination of pyrrolo[1,2-a]quinoxalines?

Organic & Biomolecular Chemistry Pub Date: 2021-05-21 DOI: 10.1039/D1OB00759A

Abstract

We report a C3–H direct iodination of pyrrolo[1,2-a]quinoxalines with TBAI or I2; a series of novel 3-iodopyrrolo[1,2-a]quinoxaline derivatives were obtained with excellent regioselectivity and broad substrate scope. Mechanism studies show that a catalytic amount of p-toluenesulfonic acid significantly promotes the selectivity and conversion of the reaction. Notably, the reaction can be performed on a gram scale, and the iodinated products can be further transformed into potentially biologically active pyrrolo[1,2-a]quinoxaline derivatives by palladium-catalyzed coupling reactions.

Graphical abstract: Highly selective C3–H iodination of pyrrolo[1,2-a]quinoxalines
Recommended Literature