Nickel-catalyzed electrochemical reductive decarboxylative coupling of <i>N</i>-hydroxyphthalimide esters with quinoxalinones

Lian, Fei; Xu, Kun; Meng, Wei; Zhang, Haonan; Tan, Zheng; Zeng, Cheng‐Chu

doi:10.1039/c9cc07840a

Cited by 71 publications

(35 citation statements)

References 46 publications

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“…After that, the generated radical intermediate 14 would be oxidized at the anode to yield the protonated product (Figure 9C). Around the same time, Zeng, Xu, and co‐workers reported an electrochemical decarboxylative coupling of NHP esters with quinoxalinones for the synthesis of 3‐alkylated quinoxalinones by using nickel as the mediator [23] …”

Section: Sequential Paired Electrolysismentioning

confidence: 99%

Reaching the Full Potential of Electroorganic Synthesis by Paired Electrolysis

Zhang

Hong

et al. 2021

The Chemical Record

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Electroorganic synthesis has recently become a rapidly blossoming research area within the organic synthesis community. It should be noted that electrochemical reaction is always a balanced reaction system with two half‐cell reactions‐oxidation and reduction. Most electrochemical strategies, however, typically focus on one of the two sides for the desired transformations. Paired electrolysis has two desirable half reactions running simultaneously, thus maximizing the overall margin of atom and energy economy. Meanwhile, the spatial separation between oxidation and reduction is the essential feature of electrochemistry, offering unique opportunities for the development of redox‐neutral reactions that would otherwise be challenging to accomplish in a conventional reaction flask setting. This review discusses the most recent illustrative examples of paired electrolysis with special emphasis on sequential and convergent processes.

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Section: Sequential Paired Electrolysismentioning

confidence: 99%

Reaching the Full Potential of Electroorganic Synthesis by Paired Electrolysis

Zhang

Hong

et al. 2021

The Chemical Record

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“…In general, NHP esters are versatile Csp 3 alkyl radical precursors and show tolerance with various functional groups. In the series of electrochemical metal‐catalyzed reactions, Zeng et al [18] . reported the first example of nickel‐catalyzed electrochemical decarboxylative coupling of NHP esters with 2‐quinoxalinones, yielding the various Csp 3 −Csp 2 coupled products under mild conditions (Scheme 4).…”

Section: Electrochemical Decarboxylative C−c Bond Formationmentioning

confidence: 99%

“…[16] However,s trong chemical oxidants such as TBHP and K 2 S 2 O 8 were neededf or the generation of alkyl radicals from alkyl radical precursors and these alkyl radical precursors were not compatible with functional group tolerances. [17] In general, NHP esters are versatile Csp 3 alkyl radicalp recursors ands how tolerance with various functional groups.I nt he series of electrochemical metal-catalyzed reactions, Zeng et al [18] reported the first example of nickel-catalyzede lectrochemicald ecarboxylative coupling of NHPe sters with 2-quinoxalinones, yielding the various Csp 3 ÀCsp 2 coupled products under mild conditions (Scheme 4). Under the optimized reaction conditions, NHP protected primary,s econdary,a nd tertiary aliphatic carboxylic acids afforded the various 3-alkylated quinoxalinones (6a-c)i ng ood to excellent yields.…”

Section: Electrochemical Decarboxylative Càcb Ond Formationmentioning

confidence: 99%

“…Based on mechanistic investigations, sodium trifluorom ethane sulfinate (17)e xperienced the anodic oxidation to form the intermediate which lost aS O 2 group rapidly and generated the CF 3 radical. Subsequently,t his highly active CF 3 radicali nteracted with cinnamic acid( 16)a nd generated the radical species that underwent decarboxylation and yielded the desired C vinyl -CF 3 product (18).…”

Section: Electrochemical Decarboxylative Csp 2 -Cf 3 Bond Formationmentioning

confidence: 99%

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Advances in Electrochemical Decarboxylative Transformation Reactions

Ramadoss

Zheng

Shao

et al. 2020

Chemistry A European J

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Owing to their non‐toxic, stable, inexpensive properties, carboxylic acids are considered as environmentally benign alternatives as coupling partners in various organic transformations. Electrochemical mediated decarboxylation of carboxylic acid has emerged as a new and efficient methodology for the construction of carbon‐carbon or carbon‐heteroatom bonds. Compared with transition‐metal catalysis and photoredox catalysis, electro‐organic decarboxylative transformations are considered as a green and sustainable protocol due to the absence of chemical oxidants and strong bases. Further, it exhibits good tolerance with various functional groups. In this Minireview, we summarize the recent advances and discoveries on the electrochemical decarboxylative transformations on C−C and C−heteroatoms bond formations.

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“…Zeng and co-workers developed a method of Ni-catalyzed electrochemical reductive coupling of NHP esters with quinoxalinones for the synthesis of 3-alkylated quinoxalinones ( Lian et al., 2019 ). Reaction condition optimization demonstrated that graphite felt and nickel foam were the optimal electrode materials and reactions were conducted in an undivided cell with Et 3 N as the sacrificial reductant.…”

Section: Electrochemical Nickel Catalysismentioning

confidence: 99%

Harnessing Radical Chemistry via Electrochemical Transition Metal Catalysis

Wang

McCallum

et al. 2020

iScience

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Summary The merger of transition metal catalysis and electroorganic synthesis has recently emerged as a versatile platform for the development of highly enabling radical reactions in a sustainable fashion. Electrochemistry provides access to highly reactive radical species under extremely mild reaction conditions from abundant native functionalities. Transition metal catalysts can be used as redox-active electrocatalysts to shuttle electrons, chiral information to organic substrates, and the reactive intermediates in the electrolytic systems. The combination of these strategies in this mechanistic paradigm thus makes the generation and utilization of radical species in a chemoselective manner and allows further application to more synthetically attractive enantioselective radical transformations. This perspective discusses key advances over the past few years in the field of electrochemical transition metal catalysis and demonstrates how the unique features of this strategy permit challenging or previously elusive transformations via radical pathways to be successfully achieved.

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Nickel-catalyzed electrochemical reductive decarboxylative coupling of N-hydroxyphthalimide esters with quinoxalinones

Abstract: The first example of electrochemically enabled, NiCl2-catalyzed reductive decarboxylative coupling of N-hydroxyphthalimide esters with quinoxalinones was developed.

Cited by 71 publications

References 46 publications

Reaching the Full Potential of Electroorganic Synthesis by Paired Electrolysis

Reaching the Full Potential of Electroorganic Synthesis by Paired Electrolysis

Advances in Electrochemical Decarboxylative Transformation Reactions

Harnessing Radical Chemistry via Electrochemical Transition Metal Catalysis

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