A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

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

doi:10.1039/c8ra04407d

Cited by 51 publications

(29 citation statements)

References 26 publications

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“…And obviously, for same 5‐substituted 3,4‐dihalogen‐2(5 H )‐furanones 1 , the yield of the target product obtained from 2b as a substrate is lower than that using 2a (e.g., 5a vs. 3a , 5b vs. 3b , 5c vs. 3j , 5d vs. 3m , 5e vs. 4a , 5f vs. 4b , 5g vs. 4i ). This effect is similar to the results of arylselenocyanation reported previously . In addition, the chemical structures of the obtained products 5 have been confirmed by X‐ray analysis of 5d (see the SI for details) .…”

Section: Resultssupporting

confidence: 87%

C4‐Selective Synthesis of Vinyl Thiocyanates and Selenocyanates Through 3,4‐Dihalo‐2(5H)‐furanones

Yang

Luo

et al. 2019

Eur J Org Chem

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In the absence of a metal catalyst and under the promotion of sodium bicarbonate, an eco‐friendly and practical protocol for the synthesis of vinyl thiocyanate derivatives through the reaction of 3,4‐dihalo‐2(5H)‐furanones with KSCN at room temperature has been developed. This method has a broad substrate scope and is suitable for gram‐scale synthesis (up to 5 g). Importantly, it can also be used to synthesize vinyl selenocyanate derivatives.

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Section: Resultssupporting

confidence: 87%

C4‐Selective Synthesis of Vinyl Thiocyanates and Selenocyanates Through 3,4‐Dihalo‐2(5H)‐furanones

Yang

Luo

et al. 2019

Eur J Org Chem

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“…The heterolysis of RSeI then generates the strong electrophile RSe + which is prone to selenate indole. Other electrochemical indole functionalizations including halogenation, thio‐ and selenocyanation, sulfenylation and sulfonylation have also been developed recently.…”

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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“…Based on these experimental results and previous repo rts, [52][53][54][55][56][57][58][59][60] a possible mechanism for the thiocyanation of αamino carbonyl compounds is proposed (Scheme 3). Initially, + SCN is formed from the KSCN by the oxidant and adds to the substrate 1a to afford intermediate I.…”

Section: Resultsmentioning

confidence: 64%

Thiocyanation of α-amino carbonyl compounds for the synthesis of aromatic thiocyanates

Ouyang

Liu

et al. 2020

Journal of Chemical Research

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A procedure for K2S2O8-mediated thiocyanation of α-amino carbonyl compounds has been developed for the synthesis of aromatic thiocyanates. A series of α-amino carbonyl compounds have been investigated, and the desired products are obtained in 74%–93% yields. This strategy has the advantages of simple reaction conditions without use of a transition-metal catalyst, high regioselectivity, and high efficiency. Moreover, we found that arylamine thiocyanates can also be obtained from α-amino carbonyl compounds and potassium thiocyanate in the presence of CoCl2·6H2O, I2, and dimethyl sulfoxide through the cleavage of the C–N bond. To explore the reaction mechanism, we designed several control experiments and proposed a possible mechanism using the experimental results and related literature reports.

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A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

Cited by 51 publications

References 26 publications

C4‐Selective Synthesis of Vinyl Thiocyanates and Selenocyanates Through 3,4‐Dihalo‐2(5H)‐furanones

C4‐Selective Synthesis of Vinyl Thiocyanates and Selenocyanates Through 3,4‐Dihalo‐2(5H)‐furanones

Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives

Thiocyanation of α-amino carbonyl compounds for the synthesis of aromatic thiocyanates

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