Phosphorous acid–assisted electrochemical α-tetrahydrofuranylation of sulfonamides and amides

Abstract

Tetrahydrofuran rings are present in a wide variety of biologically active molecules, which highlights the importance of developing a mild, convenient method for synthesizing compounds bearing these rings. Herein, we...

Visible-Light-Promoted α-C(sp3)–H Amination of Ethers with Azoles and Amides

“…In 2023, Wang's group developed an efficient electrochemical protocol for phosphorous acid−assisted amination of tetrahydrofuran with amides (Scheme 3a) via a direct radical cross-coupling process. 22 Here, we report the first example of direct coupling reactions between alkyl CCRs and NCRs, promoting the highly regioselective condensation of ethers with azoles or amides via photocatalysis. The developed method shows a broad substrate scope by the photocatalytic process (Scheme 3b).…”

“…Due to the high activity of alkyl CCRs and NCRs, their direct coupling reaction has rarely been reported. In 2023, Wang’s group developed an efficient electrochemical protocol for phosphorous acid–assisted amination of tetrahydrofuran with amides (Scheme a) via a direct radical cross-coupling process . Here, we report the first example of direct coupling reactions between alkyl CCRs and NCRs, promoting the highly regioselective condensation of ethers with azoles or amides via photocatalysis.…”

Recent advances in electrochemical C–H bond amination

“…An alternative approach reported by Wang's team in 2023 showed the electrochemical amination of tetrahydrofuran assisted by H 3 PO 3 . 51 In the proposed mechanism (Scheme 13b), TsNH 2 played a dual role. On the one hand, it lost an electron to release radical cation 18A , which was deprotonated to the reactive radical 18B ; on the other hand, 18A simultaneously helped generate a radical intermediate from tetrahydrofuran via mediated oxidation.…”

Electrochemical dehydroxymethylative functionalization of alkanols for forging C(sp3)–heteroatom bonds

“…5 Lei, Xu, Lambert, and others separately reported benzylic C(sp 3 )–H amination and azolation reactions under electrochemical conditions, which has greatly enriched the synthetic protocols for the construction of C(sp 3 )–N bonds. 6 In addition, Lee and co-workers described an elegant work for the carbocationic activation of alkylboron reagents to introduce a series of heteroatoms attached to sp 3 -carbons. 7…”