Cyclization Reactions of Anode-Generated Amidyl Radicals

Xu, Hai‐Chao; Campbell, John M.; Moeller, Kevin D.

doi:10.1021/jo402623r

Cited by 111 publications

(49 citation statements)

References 73 publications

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“…The generation of amidyl radicals by oxidative cleavage of the nitrogen–hydrogen bond is highly desirable due to the lack of pre‐functionalization. Electro‐organic chemistry is able to engage this issue by mediated or direct oxidation at the anode. Recently, we reported a methodology to afford amidyl radicals by direct oxidation in order to construct five‐ and six‐membered heterocycles by dehydrogenative N,N coupling reactions .…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Synthesis of 5‐Aryl‐phenanthridin‐6‐one by Dehydrogenative N,C Bond Formation

Kehl

Breising

Schollmeyer

et al. 2018

Chemistry A European J

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Currently, the general synthesis of 5‐aryl‐phenanthridin‐6‐ones relies on the involvement of metal catalysis. Despite the urgent demand for green alternatives, avoiding synthetic routes that require transition metals for key roles is still challenging. Electrochemical efforts employing a constant potential protocol in divided cells revealed a possible alternative to the catalytic approach. A constant current protocol, undivided cells, and a remarkably low supporting electrolyte concentration enable a novel access to N‐aryl‐phenanthridin‐6‐ones by anodic N,C bond formation using directly generated amidyl radicals. Easy accessible starting materials, a broad scope of applicable functional groups, good yields, and a very simple set‐up are the benefits of this sustainable method.

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Section: Methodsmentioning

confidence: 99%

Electrochemical Synthesis of 5‐Aryl‐phenanthridin‐6‐one by Dehydrogenative N,C Bond Formation

Kehl

Breising

Schollmeyer

et al. 2018

Chemistry A European J

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“…87 Five- and six-membered rings could be effectively forged through 5- and 6- exo attacks, respectively. The benzyloxy group on the amide lowers the oxidation potential of the amide nitrogen while stabilizing the ensuing radical species.…”

Section: Anodic Oxidationmentioning

confidence: 99%

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

2017

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“…Moeller and co-workers expanded the synthetic scope to amides and reported the first direct electrochemical generation of amidyl radicals. [122] Theu se of amides and anilides enabled the direct synthesis of lactams as valuable core structures (Scheme 37). Mechanistically,t he olefin served as the trapping group as the oxidation potential of the depro-tonated amide anion was shown to be lower in cyclic voltammetry studies.…”

Section: Electrochemical Synthesis Of Heterocyclesmentioning

confidence: 99%

Electrifying Organic Synthesis

et al. 2018

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The direct synthetic organic use of electricity is currently experiencing a renaissance. More synthetically oriented laboratories working in this area are exploiting both novel and more traditional concepts, paving the way to broader applications of this niche technology. As only electrons serve as reagents, the generation of reagent waste is efficiently avoided. Moreover, stoichiometric reagents can be regenerated and allow a transformation to be conducted in an electrocatalytic fashion. However, the application of electroorganic transformations is more than minimizing the waste footprint, it rather gives rise to inherently safe processes, reduces the number of steps of many syntheses, allows for milder reaction conditions, provides alternative means to access desired structural entities, and creates intellectual property (IP) space. When the electricity originates from renewable resources, this surplus might be directly employed as a terminal oxidizing or reducing agent, providing an ultra‐sustainable and therefore highly attractive technique. This Review surveys recent developments in electrochemical synthesis that will influence the future of this area.

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Cyclization Reactions of Anode-Generated Amidyl Radicals

Cited by 111 publications

References 73 publications

Electrochemical Synthesis of 5‐Aryl‐phenanthridin‐6‐one by Dehydrogenative N,C Bond Formation

Electrochemical Synthesis of 5‐Aryl‐phenanthridin‐6‐one by Dehydrogenative N,C Bond Formation

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

Electrifying Organic Synthesis

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