Metal-free photo-induced heteroarylations of C–H and C–C bonds of alcohols by flow chemistry. Issue 11 (18th May 2022)

• Record Type: Journal Article
• Authors: Cao, Zhu; Ji, Meishan; Wang, Xinxin; Wu, Xinxin; Li, Yahong; Zhu, Chen
• Is Part Of: Green chemistry. Volume 24:Issue 11(2022)
• Page Start: 4498
• Page End: 4503
• Publication Date: 2022-05-18
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc01144a
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Practical, metal-free heteroarylations of inert C–H and C–C bonds of unprotected aliphatic alcohols are achieved in a 'stop-flow' micro-tubing reactor, and can be readily scaled up by a continuous-flow method. Abstract : Practical, metal-free heteroarylations of C–H and C–C bonds of unprotected aliphatic alcohols are accomplished in a 'stop-flow' micro-tubing reactor. The reactions proceed through alkoxy radical-triggered hydrogen atom transfer and β-C(sp 3 )–C(sp 3 ) bond rupture under mild photochemical conditions, leading to a plethora of valuable functionalized heteroarenes. The reaction is amenable for late-stage functionalization of complex heteroarenes, and can be readily scaled up by a continuous-flow method. The protocol features many advantages including good regioselectivity, broad functional group compatibility, and easy operation, and may find potential use in medicinal chemistry.