Visible-light photoredox-catalyzed dual C–C bond cleavage: synthesis of 2-cyanoalkylsulfonylated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide

Liu, Yu; Wang, Qiaolin; Chen, Zan; Li, Hua; Zhang, Panliang

doi:10.1039/c9cc10057a

Cited by 102 publications

(20 citation statements)

References 113 publications

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“…Figure 2 c is the N 1s spectrum, which confirms that the CoFe 2 O 4 /g-C 3 N 4 composite has three kinds of nitrogen. The 398.3 eV is the sp 2 hybrid nitrogen (N1), the 399.2 eV is the tertiary nitrogen (N2), and the 400.9 eV is the amino functional group (N3), respectively [ 27 , 28 ]. The high-resolution Co 2p 3/2 spectrum presents the signals of Co 2+ , Co 3+ , and satellite ( Figure 2 d), where the presence of Co 3+ , Co 2+ , and vibration satellite are respectively exhibited by the brown main peak (780.5 eV), the blue green peak at 782.2 eV, and the peak at 786.8 eV [ 29 , 30 , 31 ].…”

Section: Resultsmentioning

confidence: 99%

Enhancing the Capacity and Stability by CoFe2O4 Modified g-C3N4 Composite for Lithium-Oxygen Batteries

Zhao

Ding

et al. 2021

Nanomaterials

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As society progresses, the task of developing new green energy brooks no delay. Li-O2 batteries have high theoretical capacity, but are difficult to put into practical use due to problems such as high overvoltage, low charge-discharge efficiency, poor rate, and cycle performance. The development of high-efficiency catalysts to effectively solve the shortcomings of Li-O2 batteries is of great significance to finding a solution for energy problems. Herein, we design CoFe2O4/g-C3N4 composites, and combine the advantages of the g-C3N4 material with the spinel-type metal oxide material. The flaky structure of g-C3N4 accelerates the transportation of oxygen and lithium ions and inhibits the accumulation of CoFe2O4 particles. The CoFe2O4 materials accelerate the decomposition of Li2O2 and reduce electrode polarization in the charge–discharge reaction. When CoFe2O4/g-C3N4 composites are used as catalysts in Li-O2 batteries, the battery has a better discharge specific capacity of 9550 mA h g−1 (catalyst mass), and the cycle stability of the battery has been improved, which is stable for 85 cycles.

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Section: Resultsmentioning

confidence: 99%

Enhancing the Capacity and Stability by CoFe2O4 Modified g-C3N4 Composite for Lithium-Oxygen Batteries

Zhao

Ding

et al. 2021

Nanomaterials

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“…Methylenecyclopropanes (MCPs) are amenable substrates for the trapping of radicals, generating intermediates that are prone to C–C cleavage. Tang and Shi deepened in these strategies based on the attack of radical species generated in situ either chemically or photochemically (for instance CF 3 [ 102 ], SCF 3 [ 103 ], alkyl [ 104 , 105 ], acyl [ 106 ], sulfonyl [ 107 , 108 ] or cyanoalkylsulfonyl radicals [ 109 ]) to the exocyclic C=C bond of the MCP, generating the opening of the cyclopropyl ring and subsequent attack of the resulting alkyl radical to the aromatic ring ( Scheme 34 ). For instance, the Ru-photocatalyzed approach to the synthesis of 3-sulfonyl-1,2-dihydronaphthalenes 274 employed (cyclopropylidenmethyl)benzene derivatives 267 and aryl or alkyl sulfonylchlorides as starting materials, in the presence of 5 mol% of [Ru(bpy) 3 Cl 2 ] catalyst under blue LED irradiation.…”

Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

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“…Recently, Tang and co‐workers reported a photoredox‐catalyzed radical cascade cyclization between cycloketone oxime esters 177 , methylenecyclopropanes 178 and K 2 S 2 O 5 (Scheme 61). [78] The reaction involved dual C−C bond cleavage, sulfur dioxide insertion and intramolecular cyclization, affording structurally diverse cyanoalkylsulfonated 3,4‐dihydronaphthalenes 179 with the yields in the range of 67–89%. In general, methylenecyclopropanes bearing electron‐donating substituents were superior to that bearing electron‐withdrawing substituents in the transformation.…”

Section: Photocatalyzed Cross‐couplings Reactionsmentioning

confidence: 99%

Recent Developments in Radical Cross‐Coupling of Redox‐Active Cycloketone Oximes

2020

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Recent years have witnessed a renaissance of radical cross‐coupling of cycloketone oximes which served as active cyanoalkyl radical via ring fragmentation in various transformations. It provided an efficient and practical strategy to introduce cyanoalkyl groups into organic compounds without using toxic cyanide sources. In this review, a comprehensive overview of recent advances in the field of redox‐active cycloketone oximes‐based cross‐couplings were covered. This review was categorized into two broad parts: non‐photocatalyzed and photocatalyzed cross‐couplings according to the reaction conditions. Moreover, the two broad parts were further divided into several sub‐sections depending on the nature of the bond formation. Some representative examples along with reaction mechanisms were also discussed.

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Visible-light photoredox-catalyzed dual C–C bond cleavage: synthesis of 2-cyanoalkylsulfonylated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide

Abstract: A novel visible-light photoredox-catalyzed dual C–C bond cleavage of methylenecyclopropanes and cycloketone oximes for accessing 2-cyanoalkylsulfonated 3,4-dihydronaphthalenes is established.

Cited by 102 publications

References 113 publications

Enhancing the Capacity and Stability by CoFe2O4 Modified g-C3N4 Composite for Lithium-Oxygen Batteries

Enhancing the Capacity and Stability by CoFe2O4 Modified g-C3N4 Composite for Lithium-Oxygen Batteries

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Recent Developments in Radical Cross‐Coupling of Redox‐Active Cycloketone Oximes

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