Electroauxiliary

Yosida, Jun-ichi

doi:10.1007/978-1-4419-6996-5_344

Cited by 5 publications

(2 citation statements)

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“…The use of silanes (or trialkyltin) α to heteroatoms (e.g., N, O, and S) results in raising the HOMO energy and thus facilitating oxidative radical generation; examples include α-amino silanes, α-silyl ethers, and α-silylthioethers. , The oxidation potential relative to the des-silyl analog is largest in magnitude for O as the α-heteroatom and smallest for S (see Scheme ). − The generation of radicals can also be accomplished via HAT, − including those via oxidative proton-coupled electron transfer or reductive PCET. − …”

Section: Basics Of Electrochemistry and Photoredox Catalysismentioning

confidence: 99%

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

2021

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Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do electrochemistry and photoredox catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) that enable bond formations not constrained by the rules of ionic or 2 electron (e) mechanisms. Instead, they enable 1e mechanisms capable of bypassing electronic or steric limitations and protecting group requirements, thus enabling synthetic chemists to disconnect molecules in new and different ways. However, while providing access to similar intermediates, electrochemistry and photoredox catalysis differ in several physical chemistry principles. Understanding those differences can be key to designing new transformations and forging new bond disconnections. This review aims to highlight these differences and similarities between electrochemistry and photoredox catalysis by comparing their underlying physical chemistry principles and describing their impact on electrochemical and photochemical methods.

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Section: Basics Of Electrochemistry and Photoredox Catalysismentioning

confidence: 99%

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

2021

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“…(3) Electroauxiliaries: Attachment of suitable functional groups to control the reactivity of substrate molecules and reaction pathways has often been used in organic synthesis. Such an approach based on intramolecular control includes use of directing groups, protecting groups, and chiral auxiliaries.…”

Section: Introductionmentioning

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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