Metal-free C-3 selective C(sp2)-C(sp3) heteroarylation of anilines with imidazo[1,2- a]pyridine derivatives via cross-dehydrogenative coupling

Kai Wang; Xiaoxue Du; Pengfei Zhang; Zhenjiang Wei; Xian-Ting Cao

doi:10.1039/d3ra03852a

Metal-free C-3 selective C(sp²)-C(sp³) heteroarylation of anilines with imidazo[1,2- a]pyridine derivatives via cross-dehydrogenative coupling

RSC Adv. 2023 Jul 19;13(31):21685-21689. doi: 10.1039/d3ra03852a. eCollection 2023 Jul 12.

Authors

Kai Wang¹, Xiaoxue Du¹, Pengfei Zhang², Zhenjiang Wei³, Xian-Ting Cao¹

Affiliations

¹ College of Medical Engineering & the Key Laboratory for Medical Functional Nanomaterials, Jining Medical University Jining 272067 China chemcxt@mail.jnmc.edu.cn.
² College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University Hangzhou 311121 China.
³ Department of Pharmaceutical Engineering, Shandong Medicine Technician College Taian 271016 China tianyiwzj@126.com.

Abstract

A general and straightforward method for the regioselective construction of C-3 heteroaryl-containing imidazo[1,2-a]pyridines via cross-dehydrogenative coupling under transition-metal-free conditions has been reported, utilizing N,N-dimethylaniline as the methylenation source and furnishing the C(sp²)-C(sp³) functionalized products in good to excellent yields. Mechanism studies indicate that a radical pathway is responsible for this transformation.