Electrochemical Synthesis of 1,2,4‐Thiadiazoles through Intermolecular Dehydrogenative S‐N Coupling

Li, Jiang-Sheng; Xie, Xin-Yun; Yang, Pan‐Pan; Jiang, Si; Li, Tao; Li, Zhiwei; Lu, Chunmei; Liu, Weidong

doi:10.1002/adsc.201901290

Cited by 32 publications

(12 citation statements)

References 60 publications

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“…[49] Li and co-workers illustrated the electrochemical intermolecular coupling reaction of isothiocyanates with 2-aminopyridines to access to 1,2,4-thiadiazloes (Scheme 28). [50] The n-Bu 4 NI served the both role of catalyst and electrolyte obviating use of external oxidants and transition-metal catalysts. Good functional group was tolerated in moderate to excellent yield.…”

Section: Electrochemical Non-dehydrogenative Sà N Bond Formationmentioning

confidence: 99%

Electrochemical Heteroatom‐Heteroatom Bond Construction

Gao

et al. 2021

The Chemical Record

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Heteroatom-heteroatom linkage, with SÀ S bond as a presentative motif, served a crucial role in biochemicals, pharmaceuticals, pesticides, and material sciences. Thus, preparation of the privileged scaffold has always been attracting tremendous attention from the synthetic community. However, classic protocols suffered from several drawbacks, such as toxic and unstable agents, poor functional group tolerance, multiple steps, and explosive oxidizing regents as well as the transitional metal catalysts. Electrochemical organic synthesis exhibited a promising alternative to the traditional chemical reaction due to the sustainable electricity can be employed as the traceless redox agents. Hence, toxic and explosive oxidants and/or transitional metals could be discarded under mild reaction with high efficiency. In this context, a series of electrochemical approaches for the construction of heteroatom-heteroatom bond were reviewed. Notably, most of the cases illustrated the dehydrogenative feature with the clean energy molecules hydrogen as the sole by-product.

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Section: Electrochemical Non-dehydrogenative Sà N Bond Formationmentioning

confidence: 99%

Electrochemical Heteroatom‐Heteroatom Bond Construction

Gao

et al. 2021

The Chemical Record

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“…Liu and co‐workers [39] reported the electrochemical intermolecular dehydrogenative coupling for the synthesis of 1,2,4‐thiadiazoles starting from isothiocyanates and 2‐aminopyridines utilizing n ‐Bu 4 NI as a source of iodide mediator as well as supporting electrolyte, wherein the N ‐iodopyridin‐2‐amine is proposed to be the crucial active species (Scheme 28). Both electron‐rich substituents as well as 2‐aminopyridines along with aryl and aliphatic isothiocyanates provided the desired products in good yields.…”

Section: Non‐metallic Redox Mediator Merged With Electrosynthesismentioning

confidence: 99%

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

2021

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Embracing sustainable green methodologies and techniques in chemical transformations has always been in the limelight to the synthetic community. Electrosynthesis has emerged as a powerful, sustainable synthetic tool for molecular synthesis exploiting inexpensive electricity in place of sacrificial chemical oxidizing/reducing reagents. Herein, recent advances in the incorporation of transition metal‐free redox mediators in electrosynthesis for the construction of C−N bonds are outlined. Furthermore, conjugation of this strategy with flow catalysis allows easy scale up of the synthesis of molecular assembly. This comprehensive Review provides an overview of metal‐free mediated electro‐construction of C−N bonds, focusing on the reaction mechanisms involved and its synthetic applications.

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“…27 1,2,4-thiadiazoles have been synthesized by various methods, like copper-catalyzed reaction of amidine hydrochlorides with isothiocyanates, 28 from aryl nitriles in 1-butyl-3-methylimidazolium bromide, 29 molecular iodine catalyzed N─S bond formation, 30 copper-catalyzed aerobic oxidative annulation, 31 and electrochemical intermolecular dehydrogenative S─N coupling. 32 Despite these interesting reports for synthesis of these moieties, visible light promoted methods for synthesis of 1,2,4-thiadiazoles remains a relatively unexplored area. Accordingly, in persistence of our current research attention on the incorporating the newer alternatives to access biologically vital heterocyclic moieties in an eco-friendly green method, [33][34][35] in present study, we herein devise a novel, photocatalyed, metal-free, clean and efficient synthesis of 1,2,4thiadiazoles nucleus using organic dye eosin Y as a photoredox catalyst (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Visible light promoted formation of N─S bond by photocatalyst Eosin Y

Verma

Srivastava

Tiwari

et al. 2020

Journal of Heterocyclic Chem

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A novel efficient protocol for the synthesis of 5‐imino‐1,2,4‐thiadiazole motif in open air and visible light has been reported. The reaction involves Eosin Y as photocatalyst which is a cost‐effective organic dye. The designed protocol represents a novel, mild, metal free, green strategy for the construction of 1,2,4‐thiadiazole nucleus by intramolecular cyclization via N─S bond formation. The reaction has been carried out under visible light exposure in ethanol: water (4:1) mixture using 2‐aminopyridine and isocyanate as reactants.

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Electrochemical Synthesis of 1,2,4‐Thiadiazoles through Intermolecular Dehydrogenative S‐N Coupling

Cited by 32 publications

References 60 publications

Electrochemical Heteroatom‐Heteroatom Bond Construction

Electrochemical Heteroatom‐Heteroatom Bond Construction

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

Visible light promoted formation of N─S bond by photocatalyst Eosin Y

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