Biomimetic photocatalytic sulfonation of alkenes to access β-ketosulfones with single-atom iron site

Wen, Jiangwei; Yang, Xiaoting; Sun, Zongzhao; Yang, Jianjing; Han, Peng; Qiuxia, Liu; Dong, Hongyan; Gu, Meng; Huang, Limin; Wang, Hua

doi:10.1039/c9gc03580j

Cited by 60 publications

(45 citation statements)

References 50 publications

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“…Wen et al adopted a facile molecule coupling approach to fabricate carbon nitride-hemin (CNH) composite photocatalyst. 79 The atomic-resolution HAADF-STEM image of CNH exhibits the bright spots with sizes of ca . 0.20 nm, ascribed to the loading of single atom Fe on CNH.…”

Section: Single-atom Photocatalysts For Emerging Redox Reactionsmentioning

confidence: 99%

“… 32 , 34 , 47 , 50 , 59 , 75 In contrast, there are fewer works on the application of single-atom photocatalysts for emerging reactions to generate the value-added chemicals and/or energy sources, such as H 2 O 2 , 38 phenol, 76 imines, 77 syngas (CO and H 2 ), 78 HDN, 42 and β-ketosulfones. 79 In this contribution, for the first time we review and discuss the recent progress in the design and fabrication of single-atom photocatalysts for a variety of emerging reactions, which are categorized into three different types: (i) reduction reactions, (ii) oxidation reactions, and (iii) redox reactions. The structure–performance relationships for some specific reactions on single-atom photocatalysts are discussed and summarized.…”

Section: Introductionmentioning

confidence: 99%

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Single-Atom Photocatalysts for Emerging Reactions

et al. 2021

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Single-atom photocatalysts have demonstrated an enormous potential in producing value-added chemicals and/or fuels using sustainable and clean solar light to replace fossil fuels causing global energy and environmental issues. These photocatalysts not only exhibit outstanding activities, selectivity, and stabilities due to their distinct electronic structures and unsaturated coordination centers but also tremendously reduce the consumption of catalytic metals owing to the atomic dispersion of catalytic species. Besides, the single-atom active sites facilitate the elucidation of reaction mechanisms and understanding of the structure-performance relationships. Presently, apart from the well-known reactions (H2 production, N2 fixation, and CO2 conversion), various novel reactions are successfully catalyzed by single-atom photocatalysts possessing high efficiency, selectivity, and stability. In this contribution, we summarize and discuss the design and fabrication of single-atom photocatalysts for three different kinds of emerging reactions (i.e., reduction reactions, oxidation reactions, as well as redox reactions) to generate desirable chemicals and/or fuels. The relationships between the composition/structure of single-atom photocatalysts and their activity/selectivity/stability are explained in detail. Additionally, the insightful reaction mechanisms of single-atom photocatalysts are also introduced. Finally, we propose the possible opportunities in this area for the design and fabrication of brand-new high-performance single-atom photocatalysts.

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Section: Single-atom Photocatalysts For Emerging Redox Reactionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Single-Atom Photocatalysts for Emerging Reactions

et al. 2021

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“…In 2014, Yang, Huang, Wang and co-workers reported a photocatalytic sulfonation of alkenes to β-ketosulfones (widely used in the synthesis of compounds with biological activities [44]), using porphyrins supported in CN materials (Scheme 17) [45]. The thermal decomposition of urea at 550 °C for 2 h afforded the CN polymer, which possesses abundant -NH 2 functional groups.…”

Section: O 4 (C 48 N 4 O 8 H 26 ) 3 )mentioning

confidence: 99%

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

Silva

Bartolomeu

et al. 2020

Beilstein J. Org. Chem.

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In this review we present relevant and recent applications of porphyrin derivatives as photocatalysts in organic synthesis, involving both single electron transfer (SET) and energy transfer (ET) mechanistic approaches. We demonstrate that these highly conjugated photosensitizers show increasing potential in photocatalysis since they combine both photo- and electrochemical properties which can substitute available metalloorganic photocatalysts. Batch and continuous-flow approaches are presented highlighting the relevance of enabling technologies for the renewal of porphyrin applications in photocatalysis. Finally, the reaction scale in which the methodologies were developed are highlighted since this is an important parameter in the authors’ opinion.

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“…[33] Biomimetic photocatalytic method for the synthesis of β-ketosulfones from styrenes and sulfinic acids was also proposed. [82] In some cases, sulfonylation of unsaturated compounds proceeds even in the absence of transition metals compounds and peroxide oxidizing agents. For example, pyridine-catalyzed synthesis of β-ketosulfones 136 from sulfinic acids 135 and alkynes 134 under air was developed (Scheme 65).…”

Section: Synthesis Of β-And γ-Ketosulfonesmentioning

confidence: 99%

“…A heterogeneous version of this process was realized using doped Cu 2+ zeolite imidazolate framework‐8 (ZIF‐8) as the catalyst in MeOH at room temperature: yields of β‐ketosulfones were 60–92% [33] . Biomimetic photocatalytic method for the synthesis of β‐ketosulfones from styrenes and sulfinic acids was also proposed [82] …”

Section: Sulfonylation Of Unactivated Multiple Bondsmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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Biomimetic photocatalytic sulfonation of alkenes to access β-ketosulfones with single-atom iron site

Abstract: A biomimetic photocatalyst of single-atom iron site (CNH) has been initially fabricated through coupling carbon nitride with hemin for the visible light-promoted sulfonation of alkenes to access β-ketosulfones.

Cited by 60 publications

References 50 publications

Single-Atom Photocatalysts for Emerging Reactions

Single-Atom Photocatalysts for Emerging Reactions

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

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