Anodic cyclization of dimethyl 2-(5-aryl-5-oxopentyl)malonates into the corresponding dimethyl 2-aroylcyclopentane-1,1-dicarboxylates

Okimoto, Mitsuhiro; Yamamori, Haruki; Hoshi, Masayuki; Yoshida, Takashi

doi:10.1016/j.tetlet.2013.12.104

Cited by 4 publications

(3 citation statements)

References 42 publications

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“…410 Bromide-mediated a-oxidation has also been used for accessing spiro-dihydrofuran derivatives from dimedone and aldehydes (Scheme 38). 411 Furthermore, both intermolecular 412 and intramolecular [413][414][415][416][417][418][419][420][421][422][423][424][425][426][427][428] protocols for C-C bond formation based on halide-mediated anodic oxidation of carbonyl compounds and related derivatives have also been disclosed. The Wang group has shown that iodide-mediated anodic oxidation of aryl methyl ketones can be exploited for synthesis of a-ketoesters (Scheme 39), [429][430][431] a-ketoamides (Scheme 40) 432 and isatins (Scheme 41).…”

Section: Electrochemical C-h Bond Oxygenationmentioning

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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Section: Electrochemical C-h Bond Oxygenationmentioning

confidence: 99%

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

2018

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“…a) Yoshida's synthesis of cyclopentane derivates [43] . b) Yoshida's synthesis of cyclopropane derivates [44] . c) Baran's synthesis of cyclobutane derivate [45] .…”

Section: C‐centered Radicalsmentioning

confidence: 99%

“…However, aside from the synthesis of dimethyl‐2‐aroylcyclopropane‐1,1‐dicarboxylates ( 57 ) using dimethyl 2‐(3‐oxo‐3‐arylpropyl) malonates ( 56 ) as starting materials (Scheme 6b) [43] and the mentioned cyclopentane derivates, this strategy did not allow accessing other different ring sizes from the corresponding dicarbonylic substrates. Additional investigations led to propose a mechanism [44] . The carbon vicinal to both carbonylic groups is deprotonated by the methoxy anion formed at the cathode.…”

Section: C‐centered Radicalsmentioning

confidence: 99%

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Chicas-Baños

Frontana‐Uribe

2021

The Chemical Record

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During the last decade several research groups have been developing electrochemical procedures to access highly functionalized organic molecules. Among the most exciting advances, the possibility of using free radical chemistry has attracted the attention of the most important synthetic groups. Nowadays, electrochemical strategies based on these species with a synthetic purpose are published continuously in scientific journals, increasing the alternatives for the synthetic organic chemistry laboratories. Free radicals can be obtained in organic electrochemical reactions; thus, this review reassembles the last decade's (2010–2020) efforts of the electrosynthetic community to generate and take advantage of the C‐, O‐, and N‐centered radicals’ reactivity. The electrochemical reactions that occur, as well as the proposed mechanism, are discussed, trying to give clear information about the used conditions and reactivity of these reactive intermediate species.

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Guanidinium Hydroiodide/Cumene Hydroperoxide‐Mediated Intermolecular Oxidative Coupling Reaction of β–Ketoamides with Oxindoles

et al. 2017

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The first catalytic intermolecular oxidative cross-coupling reaction between two different carbonyl compounds was achieved by using cumene hydroperoxide as an environmentally friendly, mild oxidant in the presence of a cyclic guanidinium hydroiodide derivative as a catalyst. Cross-coupling reaction between varioub ketoamides and oxindoles took place smoothly, and the corresponding 1,4-dicarbonyl compounds were obtained in 80-99% yield.

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Anodic cyclization of dimethyl 2-(5-aryl-5-oxopentyl)malonates into the corresponding dimethyl 2-aroylcyclopentane-1,1-dicarboxylates

Cited by 4 publications

References 42 publications

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

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

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Guanidinium Hydroiodide/Cumene Hydroperoxide‐Mediated Intermolecular Oxidative Coupling Reaction of β–Ketoamides with Oxindoles

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