From Molecules to Molecular Surfaces. Exploiting the Interplay Between Organic Synthesis and Electrochemistry

Jing, Qiwei; Moeller, Kevin D.

doi:10.1021/acs.accounts.9b00578

Cited by 92 publications

(33 citation statements)

References 59 publications

(42 reference statements)

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“…The above reaction parameters ultimately led to a difference in the concentration of NCR B . Moreover, the graphite electrode exhibited a greater paramagnetic nature than the other tested electrode, resulting in increased attraction of the radical species to the graphite surface, thereby promoting oxidation of the second electron …”

Section: Preliminary Mechanism Investigationmentioning

confidence: 99%

Tunable Electrochemical C−N versus N−N Bond Formation of Nitrogen‐Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications

Han

Wang

et al. 2020

Angewandte Chemie

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Herein, an environmentally friendly electrochemical approach is reported that takes advantage of the captodative effect and delocalization effect to generate nitrogen‐centered radicals (NCRs). By changing the reaction parameters of the electrode material and feedstock solubility, dearomatization enabled a selective dehydrogenative C−N versus N−N bond formation reaction. Hence, pyrido[1,2‐a]benzimidazole and tetraarylhydrazine frameworks were prepared through a sustainable transition‐metal‐ and exogenous oxidant‐free strategy with broad generality. Bioactivity assays demonstrated that pyrido[1,2‐a]benzimidazoles displayed antimicrobial activity and cytotoxicity against human cancer cells. Compound 21 exhibited good photochemical properties with a large Stokes shift (approximately 130 nm) and was successfully applied to subcellular imaging. A preliminary mechanism investigation and density functional theory (DFT) calculations revealed the possible reaction pathway.

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Section: Preliminary Mechanism Investigationmentioning

confidence: 99%

Tunable Electrochemical C−N versus N−N Bond Formation of Nitrogen‐Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications

Han

Wang

et al. 2020

Angewandte Chemie

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“…Organic electrosynthesis, which can realize redox transformations in the absence of exogenous oxidant or reductant, has proved one of the most sustainable approaches for constructing complex molecules. [1][2][3][4][5][6] Over the past two decades, tremendous efforts have been put into this attractive field, and considerable achievements have been made. [7][8][9][10][11][12][13] Nevertheless, in most cases of the developed electrochemical reactions, only either the oxidation or reduction process can result in the expected product, while the concomitant half-reaction that takes place at the counter electrode is essentially a sacrificial reaction (Figure 1A and 1B), which makes it pretty much less-sustainable.…”

Section: Introductionmentioning

confidence: 99%

Radical–Radical Cross-Coupling Assisted N–S Bond Formation Using Alternating Current Protocol

Yuan

Wang

et al. 2022

CCS Chem

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Alternating current (AC) electrolysis is a promising, yet challenging, and under-developed protocol in organic synthesis. To achieve as high atom-efficiency as possible and avoid the use of external oxidant, the electrochemistry has become a standard organic synthesis tool. Herein, AC-based protocol is a superior option than its counterpart (DC: direct current), especially for those reactions that cannot be accomplished by DC.With an aim to achieve this objective, we have employed the AC electrolysis successfully to deliver the unprecedented cross-coupling of sulfonyl or acyl substituted aniline derivatives with thiophenols/thiols under exogenous-oxidant-and catalyst-free conditions. Numerous N-S bonds containing compounds (Total 40 number) have been prepared in up to 93% yield and good selectivity. Interestingly, no reactivity has been noted using DC electrolysis or traditional chemical approaches under our reaction conditions. Mechanistic studies indicated that disulfide is the key intermediate in this alternating current mediated radical-radical crosscoupling reaction. Therefore, the current work does not only provide an efficient method for N-S bonds formation, but also pave new sustainable avenues to innovation in organic synthesis.

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“…During the last decade, electrochemistry has received renewed interest as a tool for synthetic chemistry. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] This is exemplified by whole journal issues being dedicated to synthetic electrochemistry. 18,19 Electrochemistry offers a very mild and atom efficient method to achieve selective oxidative or reduc-tive transformations using electrons as reactants.…”

Section: Introductionmentioning

confidence: 99%

Making electrochemistry easily accessible to the synthetic chemist

et al. 2020

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From Molecules to Molecular Surfaces. Exploiting the Interplay Between Organic Synthesis and Electrochemistry

Abstract: CONSPECTUS: For many years, we have been looking at electrochemistry as a tool for exploring, developing, and implementing new synthetic methods for the construction of organic molecules. Those efforts examined electrochemical

Cited by 92 publications

References 59 publications

Tunable Electrochemical C−N versus N−N Bond Formation of Nitrogen‐Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications

Tunable Electrochemical C−N versus N−N Bond Formation of Nitrogen‐Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications

Radical–Radical Cross-Coupling Assisted N–S Bond Formation Using Alternating Current Protocol

Making electrochemistry easily accessible to the synthetic chemist

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