The electrochemically selective C3-thiolation of quinolines

Wang, Da‐Han; Zhang, Li; Xiao, Fuhong; Mao, Guojiang; Deng, Guo‐Jun

doi:10.1039/d2qo00148a

Cited by 22 publications

(12 citation statements)

References 98 publications

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“…Evidently, an electron transfer from 2a , 2b or the counter anion Br − to 1aj / 1a is thermodynamically unfeasible, thus ruling out the initiation of the reaction by a single electron transfer (SET) mechanism. 12 Consequently, we assume that the radical addition is most likely the operative pathway.…”

Section: Resultsmentioning

confidence: 99%

“…In 2022, Deng et al first disclosed the C3-thioarylation of quinolines via an electrochemical protocol. 12 Stoichiometric BF 3 •OEt 2 was required here to facilitate the reduction of quinoline to the radical anion to react with a series of thiols/thiophenols (Scheme 1B). Soon after, Wang's group reported an elegant B(2,4,6-F 3 C 6 H 2 ) 3 -catalyzed one-pot, three-step tandem process for the C3-selective C-H trifluoromethylthiolation of pyridines and quinolines in the presence of stoichiometric HBPin.…”

Section: Introductionmentioning

confidence: 99%

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C3-selective C–H thiolation of quinolines via an N-arylmethyl activation strategy

Tang

et al. 2023

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

C3-selective C–H thiolation of quinolines via an N-arylmethyl activation strategy

Tang

et al. 2023

Org. Chem. Front.

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“…A wide range of quinolines 169 are sulfenylated regioselectively at the 3 d position under the action of electric current (Scheme 73). [198] Undivided cell equipped with platinum electrodes, MeCN as the solvent, and inert atmosphere are required for this process. Presumably, BF 3 ⋅ Et 2 O additive is responsible for the high regioselectivity of the process.…”

Section: Radical Functionalization Of Heterocyclesmentioning

confidence: 99%

CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals

et al. 2023

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In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via the free-radical addition to carbon-carbon π-bonds. In these processes, intermolecular free-radical attack on the aromatic substrates represents a challenge due to relatively high resistance of aromatic π-system to addition reactions in comparison to alkene C=C bonds. The free-radical functionalization of heterocycles is especially interesting due to the diversity of their structures and chemical properties as well as their importance for medicinal chemistry, agrochemistry, and materials science. Addition of C-centered radicals to heterocycles is widely known as the Minisci-type reactions and well-reviewed. In this paper, we have summarized the main achievements in less explored group of processes: functionalization of heterocycles by intermolecular addition of heteroatom-centered radicals (O-, N-, S-/Se-, and P-radicals) with the emphasis on the papers published after 2010. Literature analysis revealed the strong trend towards the usage of electrochemistry and photoredox-catal-ysis for the generation of free radicals in recent years. The remaining fundamental problem in this field is the lack of strong experimental support for the proposed mechanisms and frequent existence of several plausible reaction pathways. The progress in mechanistic studies can significantly improve the prediction of optimal reaction conditions depending on the substrates structure. 1. Introduction 2. Radical Functionalization of Heterocycles 2.1. Reactions with the Formation of CÀ O Bonds 2.2. Reactions with the Formation of CÀ N Bonds 2.3. Reactions with the Formation of CÀ S and CÀ Se Bonds 2.4. Reactions with the Formation of CÀ P Bonds 3. Conclusions

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“…The products of such transformations can also be applied in synthetic chemistry and possess promising biological properties. Two main directions exist in this field: sulfenylation [23][24][25][26][27][28] and sulfonylation [29][30][31][32] processes. Thiols are usually applied as sulfenylating agents for various unsaturated compounds (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

Disulfides as versatile starting reagents: effective sulfonylation of alkenes with disulfides under electrochemical conditions

Mulina

Doronin

et al. 2023

Org. Chem. Front.

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The electrochemically selective C3-thiolation of quinolines

Abstract: An electrochemical method has been developed to achieve C3-thiolation of quinoline compounds. This new strategy highlights the maximum atom economy, direct conversion and also the use of simple and readily...

Cited by 22 publications

References 98 publications

C3-selective C–H thiolation of quinolines via an N-arylmethyl activation strategy

C3-selective C–H thiolation of quinolines via an N-arylmethyl activation strategy

CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals

Disulfides as versatile starting reagents: effective sulfonylation of alkenes with disulfides under electrochemical conditions

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