C–H heteroarylation of aromatics via catalyst free SN2′ coupling cycloaromatization. Issue 11 (18th May 2022)

• Record Type: Journal Article
• Authors: Lu, Qixing; Wang, Tao; Wu, Qian; Cheng, Lijing; Luo, Han; Liu, Lei; Chu, Guobiao; Wang, Lufeng; Li, Baosheng
• Is Part Of: Green chemistry. Volume 24:Issue 11(2022)
• Page Start: 4399
• Page End: 4404
• Publication Date: 2022-05-18
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc00467d
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : We have developed C–H heteroarylation of aromatics via a catalyst free SN 2′ coupling heterocycloaromatization that could realize the late-stage modification of various marketed pharmaceuticals or functional materials. Abstract : The construction of a carbon–carbon bond is the most fundamental aspect of synthetic chemistry. In this study, we developed a catalyst-free SN 2′ reaction of β-OTf-substituted enamides with aromatics to obtain aryl-substituted aza-1, 4-dicarbonyl compounds that can be in situ transformed into aryl-imidazole, aryl-thiazole, and aryl-oxazole in one-pot operation, thus achieving C–H heteroarylation of aromatics. This simple, efficient, clean and scalable strategy, which provides difficult-to-realize biaryl products, is compatible with various aromatics having varying complexities. This method can be used for the late-stage modification of various commercial pharmaceuticals or functional materials and offers an orthogonal approach for constructing biaryl compounds.