An efficient electrochemical synthesis of β-keto sulfones from sulfinates and 1,3-dicarbonyl compounds

Pan, Xiaojun; Yuan, Gaoqing

doi:10.1016/j.tet.2015.06.063

Cited by 40 publications

(17 citation statements)

References 34 publications

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“…256 Similarly, Yuan and co-workers reported an iodide mediated electrosynthesis of β -keto sulfones. 257 In the absence of a strong nucleophile, electrogenerated α -chloro 1,3-dicarbonyls may be isolated as noted by Kakiuchi (Figure 16D). 258 Halide mediated anodic α -oxidation has also been combined with Aldol and Michael reactions to furnish spirobenzofuran derivatives (Figure 16E).…”

Section: Anodic Oxidationmentioning

confidence: 66%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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Section: Anodic Oxidationmentioning

confidence: 66%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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“…In 2015, Yuan and co-workersr eported an efficient electrochemical synthesis of b-ketosulfones from sodium sulfinates and 1,3-dicarbonyl compounds with NH 4 Ia st he supportinge lectrolyte (Scheme 34). [43] Notably,C ÀCb ond cleavage occurs in this transformation. Iodide salts are necessary for this reaction because no desired product was obtained with NH 4 OAc as the supporting electrolyte.…”

Section: Synthesis Of B-keto Sulfonesf Rom Sulfinates and 13-dicarbomentioning

confidence: 90%

“…In 2015, Yuan and co‐workers reported an efficient electrochemical synthesis of β‐ketosulfones from sodium sulfinates and 1,3‐dicarbonyl compounds with NH 4 I as the supporting electrolyte (Scheme ) . Notably, C−C bond cleavage occurs in this transformation.…”

Section: C−s Bond Formation or S−x (X=n O S Se) Bond Formation Thrmentioning

confidence: 99%

Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation

Hong

Xiao

et al. 2020

ChemSusChem

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The electrolysis of organic acids has garnered increasing attention in recent years. In addition to the famous electrochemical decarboxylation known as Kolbe electrolysis, a number of other electrochemical processes have been recently established that allow for the construction of carbon–heteroatom and sulfur–heteroatom bonds from organic acids. Herein, recent advances in electrochemical C−X and S−X (X=N, O, S, Se) bond‐forming reactions from five classes of organic acids and their conjugate bases, namely, carboxylic, thiocarboxylic, phosphonic, sulfinic, and sulfonic acids, are surveyed.

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“…It was noted that the addition of radical scavangers, such as TEMPO, terminated the a-amination process and did not yield any product. Related halide-mediated procedures for cleavage of b-O-4 lignin model compounds, [984][985][986] thiocyanation 987 as well as synthesis of 3-amino-2-thiocyanato-a,b-unsaturated carbonyl derivatives 988 and b-keto sulfones 989 have also been developed. 990 Halide-mediated protocols for C-N bond coupling with alkenes have also been targeted.…”

Section: Scheme 125mentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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An efficient electrochemical synthesis of β-keto sulfones from sulfinates and 1,3-dicarbonyl compounds

Cited by 40 publications

References 34 publications

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation

Electrochemical strategies for C–H functionalization and C–N bond formation

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