Electrochemically Promoted Nickel-Catalyzed Carbon–Sulfur Bond Formation

Wang, Yang; Deng, Lingling; Wang, Xiaochen; Wu, Zheng‐Guang; Wang, Yi; Pan, Yi

doi:10.1021/acscatal.8b04633

Cited by 126 publications

(95 citation statements)

References 49 publications

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“…[38] In 2019, an ickela-electrocatalysis furthermore enabled Ullmann-typet hiolations of aryl iodides with both aryl and alkyl thiols within an on-sacrificial anode approach, as achieved by Wang and Pan (Scheme 5l). [39] In the meantime, Mei independently developed the nickelaelectrocatalyzed CÀSc ouplingo fm ore challenging aryl bromides and chlorides with aryl thiols in the absence of an external base (Scheme 5m). [40] Ap roposed mechanism for nickela-electrocatalyzed crosscouplingr eactions was suggested based on relatedn ickelaphotoredox-catalyzedc ross-couplings( Scheme 6).…”

Section: Net Redox-neutralc àHet Cross-couplingsmentioning

confidence: 99%

Evolution of High‐Valent Nickela‐Electrocatalyzed C−H Activation: From Cross(‐Electrophile)‐Couplings to Electrooxidative C−H Transformations

Zhang

Samanta

Vecchio

et al. 2020

Chemistry A European J

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C−H activation has emerged as one of the most efficient tools for the formation of carbon–carbon and carbon–heteroatom bonds, avoiding the use of prefunctionalized materials. In spite of tremendous progress in the field, stoichiometric quantities of toxic and/or costly chemical redox reagents, such as silver(I) or copper(II) salts, are largely required for oxidative C−H activations. Recently, electrosynthesis has experienced a remarkable renaissance that enables the use of storable, safe and waste‐free electric current as a redox equivalent. While major recent momentum was gained in electrocatalyzed C−H activations by 4d and 5d metals, user‐friendly and inexpensive nickela‐electrocatalysis has until recently proven elusive for oxidative C−H activations. Herein, the early developments of nickela‐electrocatalyzed reductive cross‐electrophile couplings as well as net‐redox‐neutral cross‐couplings are first introduced. The focus of this Minireview is, however, the recent emergence of nickel‐catalyzed electrooxidative C−H activations until April 2020.

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Section: Net Redox-neutralc àHet Cross-couplingsmentioning

confidence: 99%

Evolution of High‐Valent Nickela‐Electrocatalyzed C−H Activation: From Cross(‐Electrophile)‐Couplings to Electrooxidative C−H Transformations

Zhang

Samanta

Vecchio

et al. 2020

Chemistry A European J

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“…The Pan lab used a simple undivided cell setup to yield an impressively general nickel-catalyzed electrochemical thiolation reaction (Scheme 15). 55 The intermediacy of a sulfur-centered radical generated at the cathode was shown to be critical for product formation. The scope supports the intermediacy of thiyl radicals, with conjugated aryl thiols (P55, 92%) exhibiting higher yields than aliphatic thiols (P56, 63% and P57, 52%).…”

Section: Scheme 14 Electrochemically Mediated Chan-lam Reaction and Tmentioning

confidence: 99%

Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

Gale-Day¹

2020

Synthesis

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Traditionally, metal-catalyzed cross-coupling reactions rely on stable but expensive metals, such as palladium. However, the recent development of synthetic organic electrochemistry allows for in situ redox manipulations, expanding the use of cheaper, abundant and sustainable metals, such as nickel and copper as efficient cross-coupling catalysts. This short review covers the recent advances in metal-catalyzed electrochemical coupling reactions, with a focus on reactions of sp2 electrophiles and nucleophiles with sp3 coupling partners to form both C–C and C–heteroatom bonds.1 Introduction2 Nickel-Catalyzed C–C sp2–sp3 Coupling Reactions3 Coupling of Aryl Groups with Heteroatomic Nuclei4 Conclusion

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“…In 2018, Mei and co‐workers carried out a review of C−H functionalization using electrochemical transition metal catalysis and highlighted the efficiency of this combination. Very recently Pan and co‐workers described a nickel‐catalysed Ullmann‐type thiolation with a graphene foam electrode as the anode and nickel foam electrode as the cathode in an undivided cell, at a potential of 3 V in DMA at rt. Under electrosynthesis conditions, the salt NiCl 2 ⋅ glyme and the ligand 4,4′‐di‐tert‐butyl‐2,2′‐dipyridyl (dtbbpy) were mediators capable of promoting this transformation.…”

Section: Electrochemical Oxidative Cross Couplingmentioning

confidence: 99%

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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Electrochemically Promoted Nickel-Catalyzed Carbon–Sulfur Bond Formation

Cited by 126 publications

References 49 publications

Evolution of High‐Valent Nickela‐Electrocatalyzed C−H Activation: From Cross(‐Electrophile)‐Couplings to Electrooxidative C−H Transformations

Evolution of High‐Valent Nickela‐Electrocatalyzed C−H Activation: From Cross(‐Electrophile)‐Couplings to Electrooxidative C−H Transformations

Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

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

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