Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids

Bityukov, Oleg V.; Matveeva, Olesya K.; Vil, Vera A.; Kokorekin, Vladimir A.; Nikishin, G. I.; Terent’ev, Alexander O.

doi:10.1021/acs.joc.8b02791

Cited by 36 publications

(24 citation statements)

References 143 publications

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“…In 2019, Te rent'ev and co-workersr eporteda ne lectrochemically induced, intermolecular,c ross-dehydrogenative CÀOc oupling of b-diketones and b-ketoesters with carboxylic acids by using KBr as as upporting electrolyte (Scheme8). [17] They proposed that brominated b-diketones or b-ketoesters served as an important intermediates in this reaction, similart ot hat reported by Xu et al [16] Recently,W irth and co-workersr eported, for the first time, the enantioselective electrochemical lactonization of diketo acid derivatives by using chiral iodoarenes as redoxm ediators (Scheme 9). [18] Cyclic voltammetry (CV) studies show that chiral iodoarene has al ower oxidativep otentialt han that of the substrate;t his indicatest hat hypervalent iodine is first generated in situ in this electrochemical reaction and then works as ah omogeneous chiral organocatalyst to catalyzet he enantioselective lactonization reaction.…”

Section: Electrocatalytic Dehydrogenative Esterification Of Carboxylimentioning

confidence: 53%

“…In 2019, Terent'ev and co‐workers reported an electrochemically induced, intermolecular, cross‐dehydrogenative C−O coupling of β‐diketones and β‐ketoesters with carboxylic acids by using KBr as a supporting electrolyte (Scheme ) . They proposed that brominated β‐diketones or β‐ketoesters served as an important intermediates in this reaction, similar to that reported by Xu et al …”

Section: Ester C−o Bond Formation Through Electrolysis Of Carboxylic mentioning

confidence: 99%

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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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Section: Electrocatalytic Dehydrogenative Esterification Of Carboxylimentioning

confidence: 53%

Section: Ester C−o Bond Formation Through Electrolysis Of Carboxylic mentioning

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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“…In 2019, Li and Terent'ev respectively reported electrochemical bromination‐mediated esterifications between carboxylic acids with terminal alkenes or β ‐ketoester. The three‐component 1,2‐bromoesterification of alkenes involved a cyclic bromonium ion intermediate and ring‐opening process.…”

Section: Acids As Nucleophiliesmentioning

confidence: 99%

“…The three‐component 1,2‐bromoesterification of alkenes involved a cyclic bromonium ion intermediate and ring‐opening process. During the oxidative coupling of β ‐ketoester, KBr functioned as supporting electrolytes as well as the crucial promoter. As a cosolvent, H 2 O was necessary for a higher yield (Scheme ).…”

Section: Acids As Nucleophiliesmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

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The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

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“…Electrochemically‐induced C−O coupling of β ‐ketoesters with phenylacetic acid was elaborated by the Terent'ev group (Eq. 39‐1) . It achieved the generation of brominated ethyl benzoylacetate 39.2 , which underwent a substitution to give 39.1 .…”

Section: Nucleophilic Acidsmentioning

confidence: 99%

Arylacetic Acids in Organic Synthesis

et al. 2019

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Arylacetic acids are widely used in organic reactions and their recent advances are summarized in six categories according to their triggered pathways: (1) the acid as directing group in ortho-or meta-CÀ H activation; (2) decarboxylation; (3) deprotonation; (4) nucleophilic methylenes; (5) nucleophilic acids; (6) electrophilic acids. Reactions with alkenes, alkynes, aldehydes, amines, water, Grignard reagents, silanes and so forth are discussed. We hope this Minireview will promote future research in this area. Recently, the Zeng group [3g] reported a weakly coordinationassisted alkynylation of arylacetic acids with iridium catalysis under air atmosphere (Eq. 2-2). It was supported the sixmembered ring cycloiridiated 2.5 acted as the key intermediate. The alkynylation of indole, thiophene, pyrrole, and benzo[b] thiophene afforded better yields than phenylacetic acids. The acid moiety could also participated in the intramolecular ortho-CÀ H activation, which was developed by the Shi group to obtain lactonization 2.6 (Eq. 2-3) (Scheme 2). Meta-CÀ H ArylationThe study of Yu group [3e] in 2017 revealed a successful control of meta selectivity 3.1 of arylation from aryl iodides (Eq. 3-1). The use of mono-protected 3-amino-2-hydroxypyridine (as ligand) and 2-carbomethoxynorbornene (NBE-CO 2 Me) were crucial. In the absence of NBE-CO 2 Me, only ortho-arylated product was obtained. This method was still efficient in a gramsale (Scheme 3). Decarboxylation Decarboxylative CouplingAs shown in Scheme 4, the decarboxylation could generate benzyl radicals 4.1. Then, direct couplings of 4.1 with diverse [ + ] These authors contributed equally. Scheme 1. Six categories based on triggered mechanism. 2 3 4 5 6 7 8 . Passerini Three-Component ReactionThe Passerini reaction was the oldest multicomponent reaction (MCR) [37d] in which isocyanides, carboxylic acids and aldehydes were used. It was powerful for the rapid construction of complex molecules. The tactic to expand the scope of Passerini reaction was to use surrogates of the carbonyl partners. As described in Scheme 51, syn-chlorooximes, [37b] diazoketones, [37c] alcohols, [37d,e] azirines [37f] and isatins [37g] could be employed instead of aryl or alkyl aldehydes [37a] (Scheme 51). Besides, in 2018, Zhang and co-workers [37] have firstly reported asymmetric phosphoric acid-catalyzed four-component Ugi reaction, which Scheme 45. BTM-catalyzed cycloaddition. Scheme 46. HBTM-catalyzed cycloaddition. Scheme 47. TFA-catalyzed reaction. Scheme 48. Friedel-Crafts triggered tandem reactions. Scheme 49. C-acylation of 1,3-diones. Scheme 50. C-acylation of 1,3-indandiones.

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Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids

Cited by 36 publications

References 143 publications

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

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

Recent Advances of Cinnamic Acids in Organic Synthesis

Arylacetic Acids in Organic Synthesis

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