Multiple Alkylation of Thiophene Derivatives with Simple and Extended Diarylcarbenium Ion Pools

Nokami, Toshiki; Watanabe, Takashi; Terao, Ken; Soga, Kazuya; Ohata, Kousuke; Yoshida, Junichi

doi:10.5796/electrochemistry.81.399

Cited by 9 publications

(7 citation statements)

References 26 publications

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“…These cations may be trapped with carbon-centered nucleophiles such as heteroarenes, organozinc reagents, or silyl ketene acetals (Figure 17I). 288,289 Alternatively, they may be subjected to cathodic reduction where the ensuing radical was found to undergo homodimerization. Generation of the diarylcarbenium cation pool could be facilitated with silane electroaxuiliaries—this strategy also allowed the synthesis of dendritic molecules through iterative cation pool formation and nucleophile trapping (Figure 17J).…”

Section: Anodic Oxidationmentioning

confidence: 99%

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

2017

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Section: Anodic Oxidationmentioning

confidence: 99%

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

2017

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“…The resulting dendritic diarylcarbenium ions, which can be characterized by NMR spectroscopy, react with electron-rich aromatic compounds. 105 For example, dendritic diarylcarbeniun ions react with the aromatic rings of polystyrene to effect the dendronization of polystyrene (Scheme 44). 106 The dendronized polymers obtained using the firstand second-generation dendritic diarylcarbenium ions, [G-1] + and [G-2] + , respectively, were well-characterized by MALDI-TOF MS and SEC-MALLS analyses and observed by AFM.…”

Section: Stabilized Glycosyl Cationsmentioning

confidence: 99%

Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances

2017

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Electrochemistry serves as a powerful method for generating reactive intermediates, such as organic cations. In general, there are two ways to use reactive intermediates for chemical reactions: (1) generation in the presence of a reaction partner and (2) generation in the absence of a reaction partner with accumulation in solution as a "pool" followed by reaction with a subsequently added reaction partner. The former approach is more popular because reactive intermediates are usually short-lived transient species, but the latter method is more flexible and versatile. This review focuses on the latter approach and provides a concise overview of the current methods for the generation and accumulation of cationic reactive intermediates as a pool using modern techniques of electrochemistry and their reactions with subsequently added nucleophilic reaction partners.

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“…457 Diarylcarbenium ions can successfully be generated and accumulated by low-temperature electrochemical oxidation using the ''cation pool'' method. [458][459][460][461][462][463][464][465][466] In the presence of DMSO, alkoxysulfonium ions serve as the key intermediates. Treatment with a base, such as Et 3 N, or hydrolysis selectively affords the corresponding ketone 467 (Scheme 48) or alcohol 468 (Scheme 49).…”

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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Multiple Alkylation of Thiophene Derivatives with Simple and Extended Diarylcarbenium Ion Pools

Cited by 9 publications

References 26 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

Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances

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

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