Convenient synthesis of selenyl-indoles <i>via</i> iodide ion-catalyzed electrochemical C–H selenation

Zhang, Xing; Wang, Chenguang; Jiang, Hong; Sun, Linhao

doi:10.1039/c8cc04543g

Cited by 94 publications

(47 citation statements)

References 36 publications

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“…In the presence of I 2 , through anodic oxidation, the intermediate 43 is formed. On the other hand, in pathway B the intermediate 3-iodo-indole 44 is formed, similar to the mechanism proposed by Sun and co-workers (Scheme 2), [61] as previously described. After the addition of iodine, the cationic intermediate 45 reacts with sodium benzenesulfinate generating the intermediate 46.…”

Section: Electrochemical C(sp 2 )à H Chalcogenationsupporting

confidence: 84%

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

et al. 2019

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Achieving advances in the development of clean and efficient synthetic routes has become an important aim in research. In recent years, the search for new sustainable methodologies, notably environmentally benign synthetic procedures, has gained the attention of the scientific community. Electrosynthesis is a tool that has been extensively studied due to its potential application in chemical transformations and it adheres to the principles of green chemistry. Organochalogen compounds form an important class of molecules, since many of them have properties that can be applied in medicine and materials science. Thus, herein we provide a comprehensive and updated overview covering recent advances in the electrochemical C(sp2)−H bond chalcogenation of activated arenes and heterocycles as well as electrochemical chalcogenation through oxidative cross‐coupling reactions and chalcogen‐functionalization of alkenes/alkynes. The scope, limitations, and mechanisms are described and discussed, detailing the fundamental aspects and benefits of electrochemistry for the chalcogenation of organic compounds. The content of this Minireview demonstrates that it is possible to provide new synthetic routes and to improve the existing methodologies, to obtain processes more in line with current environmental protection aims. The reader will also find a discussion on the fundamental aspects and benefits of applying electrosynthesis to the assembly and operation of an electrolytic cell.

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Section: Electrochemical C(sp 2 )à H Chalcogenationsupporting

confidence: 84%

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

et al. 2019

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“…The curves of NH 4 I with 1 a (curve e) and NH 4 I with 2 a (curve f) were also measured, respectively, as shown in Figure 2, and there was no change, which indicated that I À did not oxidize the substrates in this reaction. [31] At the cathode, The COMMUNICATIONS asc.wiley-vch.de I 2 and proton are reduced to the iodine anion and hydrogen, which completes the rection cycle. At the anode, the electrochemical oxidation of I À initially results in the formation of I + by losing two electrons, which then react with olefinic alcohols to provide the iodonium cations intermediate A.…”

Section: Scheme 1 Synthesis Of O-containing Heterocyclesmentioning

confidence: 99%

“…Finally, the target product 3 and a half molar equivalent of I 2 are obtained by a rapid chemical selenation. [31] At the cathode, The COMMUNICATIONS asc.wiley-vch.de I 2 and proton are reduced to the iodine anion and hydrogen, which completes the rection cycle.…”

Section: Communications Ascwiley-vchdementioning

confidence: 99%

Electrochemical Difunctionalization of Olefines: Access to Selenomethyl‐Substituted Cyclic Ethers or Lactones

et al. 2019

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A metal-and oxidant-free electrochemical method for preparing selenomethyl-substituted cyclic ethers or lactones via difunctionalization of olefines is presented. A series of selenomethylsubstituted cyclic ethers, particularly 9-and 11membered, selenomethyl-substituted lactones (4-6 membered), and selenomethyl-substituted phthalides can be obtained via this reaction. This method features convenient operation, an electron as oxidant, and ammonium iodide as electrolyte, thereby making it a green synthesis method.

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“…Jiang, Sun and their co‐workers disclosed a transition metal‐ and oxidant‐free method for the synthesis of selenyl heteroarenes 90 with diselenides in which KI was used both as the electrolyte and the catalyst (Scheme ) . Two possible reaction pathways are potentially operative.…”

Section: Electrochemical Functionalization Of Indole Derivativesmentioning

confidence: 99%

Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives

Zhong

et al. 2020

Adv Synth Catal

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The chemists’ pursuit of the ideal synthesis and functionalization of indole derivatives has lasted over 150 years as their scaffolds have been widely found in natural products, pharmaceuticals, agrochemicals and organic materials. In this regard, the recent resurgence of adopting green and sustainable electrochemistry in organic synthesis suggests that electrosynthesis is a promising strategy. Indeed, many new intriguing applications of synthesis and functionalization of indole derivatives by direct and redox‐mediated electrochemical means have been disclosed. In this review, we highlight the fundamental aspects, reaction scopes, synthetic applications and reaction mechanisms of the electrochemical synthesis and functionalization of indole derivatives.

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Convenient synthesis of selenyl-indoles via iodide ion-catalyzed electrochemical C–H selenation

Cited by 94 publications

References 36 publications

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

Electrochemical Difunctionalization of Olefines: Access to Selenomethyl‐Substituted Cyclic Ethers or Lactones

Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives

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