Electrochemical Oxidative C—H Sulfenylation of Imidazopyridines with Hydrogen Evolution

Yuan, Yong; Cao, Yangmin; Qiao, Jinliang; Lin, Yueping; Jiang, Xiaomei; Weng, Yaqing; Tang, Shan; Lei, Aiwen

doi:10.1002/cjoc.201800405

Cited by 79 publications

(32 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In addition, C-H bonds of indole and 2-phenylimidazo[1,2-a]pyridine were successfully thiolated with aryl thiols using the developed protocol. In 2018, the Lei and Tang group reported an electrochemical oxidative C-H sulfenylation of imidazopyridines with thiols (Scheme 31) [51]. The conversion was achieved in an undivided electrolytic cell using methanol and acetonitrile as cosolvent.…”

Section: Scheme 28 C-h Sulfenylation Of 4-quinolones With Aryl Thiolsmentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Zhang

Ding

et al. 2020

Catalysts

View full text Add to dashboard Cite

The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have emerged as an important strategy to construct C-S bonds. In this review, we focus on the recent advances on the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates involving C-S bond construction.

show abstract

Section: Scheme 28 C-h Sulfenylation Of 4-quinolones With Aryl Thiolsmentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Zhang

Ding

et al. 2020

Catalysts

View full text Add to dashboard Cite

show abstract

“…In 2019, Lei and co-workers also reported the sulfenylation of imidazo[1,2-a]pyridines 1 with thiols 82 using electrochemical oxidative conditions (Scheme 53). [80] The substrate 1 bearing various functional groups reacted smoothly with alkyl/arylthiols 82 in an undivided electrolytic cell containing carbon as anode and nickel as cathode and produced the respective products 81 in 16-90% yields. The practical application of developed method was demonstrated by synthesizing the respective product in 75% (1.3 g) yield from 5 mmol of 1.…”

Section: Sulfenylation and Selenylationmentioning

confidence: 99%

Recent Advances in Radical C−H Bond Functionalization of Imidazoheterocycles

et al. 2020

View full text Add to dashboard Cite

Direct CÀ H bond functionalization through radical pathway has emerged as a powerful and ideal strategy for the synthesis of organic compounds. This review provides an overview of recent developments in radical CÀ H functionalization of imidazoheterocycles such as imidazo[1,2-a] pyridine, benzo[d]imidazo[2,1-b]thiazole, imidazo [2,1-b]thiazole, imidazo[1,2-a]pyrimidine, imidazo [2,1-a]isoquinoline, imidazo[1,2-a]pyrazine and imidazo[1,2-a]quinoline using organic peroxides, photo/electric-induced protocols, iodine-based reagents, first-row transition metal catalysts (Fe, Mn, Ni and Cu) and inorganic oxidants/or

show abstract

“…此外, 在苯亚磺酸和 α 甲基苯乙烯衍生物的交叉脱氢偶联反应中, 使用可见光驱使放氢交叉偶联的条件, 也能够顺利实现底物烯丙位的磺酰化 [51] . 而苯硫酚和富电子芳烃之间的放氢交叉偶联, 在电化学条件下亦可非常高效地进行 [52,53] . 类似的电化学策略, 也成功运用于交叉偶联放氢制备亚磺酰胺 [54] 和四取代烯烃 [55] .…”

Section: C-s 键的构筑unclassified

Cross-Coupling Hydrogen Evolution Reactions

Dong¹,

Liu²,

Wu³

2020

Acta Chim. Sinica

View full text Add to dashboard Cite

During the past decade, transition metal-catalyzed dehydrogenative cross-couplings have emerged as an attractive strategy in synthetic chemistry due to its high step-and atom-economy as well as the less functionalized coupling partners. However, such reactions have to always use stoichiometric amount of sacrificial oxidants such as peroxides, high-valent metals (Cu salts, Ag salts, etc.), or iodine(III) oxidants, thereby leading to possible generation of toxic wastes and making the process less desirable from a green chemistry perspective. The recently developed photocatalytic CCHE (cross-coupling hydrogen-evolution) reactions are a conceptually new type of reactions enabled by combination of photo-redox catalysis and proton reduction catalysis, wherein the photocatalyst uses light energy as the driving force for the cross-coupling and the hydrogen evolution catalyst may capture electrons and protons from the substrates or reaction intermediates to produce molecular hydrogen (H 2). Thus, without use of any sacrificial oxidant and under mild conditions, the dual catalyst system may afford cross-coupling products with excellent yields and an equivalent amount of H 2 as the sole byproduct. This kind of cross-coupling delivers a greener synthetic strategy and is particularly useful for reactions that involve species sensitive to traditional oxidants. In CCHE reactions, the raw materials are directly converted into products and hydrogen, the reactions are highly atom economy, environmentally friendly, and have attractive potential industrial application prospects. In this review, recent dramatic developments of photocatalytic and electrochemical CCHE reactions are discussed via the most prominent mechanistic pathways, the types of CC bond, C-X (heteroatom) bond, or X-X bond formations and specific reaction classes.

show abstract

Electrochemical Oxidative C—H Sulfenylation of Imidazopyridines with Hydrogen Evolution

Cited by 79 publications

References 56 publications

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Recent Advances in Radical C−H Bond Functionalization of Imidazoheterocycles

Cross-Coupling Hydrogen Evolution Reactions

Contact Info

Product

Resources

About