Synthetic uses of anodic substitution reactions

Eberson, Lennart; Nyberg, Klas

doi:10.1016/0040-4020(76)85132-0

Cited by 73 publications

(20 citation statements)

References 135 publications

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“…The review by Eberson and Nyberg provides a highly informative account of research in this area. 85 Electrochemistry has the advantage that aromatic hydrogens and nonactivated alkane hydrogens now can be easily functionalized. This process, C-H→C + +H + +2e -, involves anodic oxidation of a C-H bond to produce a carbenium ion which then reacts with the nitrile in the normal manner.…”

Section: Nh-co-mementioning

confidence: 99%

6.07 Ritter-Type Reactions

Bishop

2014

Comprehensive Organic Synthesis II

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Section: Nh-co-mementioning

confidence: 99%

6.07 Ritter-Type Reactions

Bishop

2014

Comprehensive Organic Synthesis II

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“…The resulting species that is generated after the initial electron transfer between an electrode and an organic substrate is subsequently diffused into solution, which is followed by a secondary reaction of the initially produced radical species. [27][28][29][30][31] Here, the potential of the electrode (E)-that is the difference between the potential at the electrode of interest and the selected reference electrode, such as the saturated calomel electrode (SCE)-will determine whether a specific electron transfer process is thermodynamically feasible, and is given by eqn (1):…”

Section: Fundamental Principles and General Considerations Of Preparamentioning

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: Methodsmentioning

confidence: 99%

“…Usually alkenes have oxidation-potentials of about 2 V, alkadienes, depending on substitution, between 1.3 V to 1.8 V [2, 3].…”

Section: Methodsmentioning

confidence: 99%

“…The halve-wave potentials were determined by graphical extrapolation. It is known from the literature that the height of the oxidation potentials of organic molecules can be correlated to their molecular shape [2].Usually alkenes have oxidation-potentials of about 2 V, alkadienes, depending on substitution, between 1.3 V to 1.8 V [2, 3].Thus it seems obvious that the ridgitity of the steroid system is directly responsible for the further lowering of the potentials of the -ene, -diene moiety in the molecules.The potentials of 7-dehydrocholesterol (la) and ergosterol (lb) are similar. One more double-bond in the side-chain of lb seems to have no influence on the potential.…”

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confidence: 99%

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