Sunlight‐Driven Synthesis of 1,2,4‐Thiadiazoles via Oxidative Construction of a Nitrogen‐Sulfur Bond Catalyzed by a Reusable Covalent Organic Framework

Yuan, Jiangpei; Xia, Qiangqiang; Zhu, Weiwei; Chao, Wu; Wang, Bingxin; Liu, Baoying; Yang, Xiaobo; Xu, Yuanqing; Xu, Hao

doi:10.1002/cptc.201900263

Cited by 21 publications

(17 citation statements)

References 62 publications

(25 reference statements)

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“…In the following year, Yang and Xu et al . reported another covalent‐organic‐framework‐ catalyzed reaction driven by sunlight to prepare 1,2,4‐thiadiazoles [14e] . In 2020, Liu, Yang, and Zhou et al.…”

Section: Methodsmentioning

confidence: 99%

H₂O₂‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature

et al. 2022

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Herein, we report the H2O2‐mediated synthesis of 1,2,4‐thiadiazole derivatives under metal‐free conditions at room temperature with ethanol as the sole solvent. Various substrates could undergo the reaction smoothly, providing the expected yields of the desired products. Moreover, the target products were obtained by filtration or extraction instead of column chromatography, which requires a large amount of organic solution and silica gel during purification. The developed synthetic method can be potentially applied in the large‐scale preparation of 1,2,4‐thiadiazole derivatives as agrochemicals, pharmaceuticals, and functional materials.

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Section: Methodsmentioning

confidence: 99%

H₂O₂‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature

et al. 2022

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“…One notable example is the use of 2D-COFs as solar photocatalysts in the synthesis of 1,2,4-thiadiazoles by cyclization of corresponding N-guanyl thioureas, N-imidoyl thioureas, and N-imidoyl thioamides, employing atmospheric oxygen as a terminal oxidant. 81 The role of the oxidant here is to abstract two protons, forming new N–S-bonds. Another reaction of particular interest is the splitting of vicinal diols into corresponding benzaldehydes by carbon nitrides in up to 20 mmol scale runs.…”

Section: Proof-of-concept Research On Organic Small Moleculesmentioning

confidence: 99%

Progress in Development of Photocatalytic Processes for Synthesis of Fuels and Organic Compounds under Outdoor Solar Light

et al. 2022

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With photovoltaics becoming a mature, commercially feasible technology, society is willing to allocate resources for developing and deploying new technologies based on using solar light. Analysis of projects supported by the European Commission in the past decade indicates exponential growth of funding to photocatalytic (PC) and photoelectrocatalytic (PEC) technologies that aim either at technology readiness levels (TRLs) TRL 1–3 or TRL > 3, with more than 75 Mio€ allocated from the year 2019 onward. This review provides a summary of PC and PEC processes for the synthesis of bulk commodities such as solvents and fuels, as well as chemicals for niche applications. An overview of photoreactors for photocatalysis on a larger scale is provided. The review rounds off with the summary of reactions performed at lab scale under natural outdoor solar light to illustrate conceptual opportunities offered by solar-driven chemistry beyond the reduction of CO 2 and water splitting. The authors offer their vision of the impact of this area of research on society and the economy.

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“…CTF-Th and CTF-Th-Ph were used for the photocatalytic synthesis of benzophosphole oxides, in presence of an external oxidant (Scheme 17) [121]. In 2019 and 2020, Yang's group [122][123][124] employed 2D-COF-1, an acylhydrazone-based COF, as photocatalytic pristine material in three different organic transformations: radical additioncyclization of 2-arylphenylisocyanides [122], C3-arylation of quinoxalinones [123] and synthesis of 1,2,4-thiadiazoles [124] (Scheme 18). In the three cases, the catalyst was recycled up to 5 times without losing its photocatalytic activity under environmentally friendly conditions.…”

Section: Other Reactionsmentioning

confidence: 99%

Metal–Organic Frameworks (MOFs) and Covalent Organic Frameworks (COFs) Applied to Photocatalytic Organic Transformations

et al. 2020

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Among the different alternatives for catalysis using metal–organic frameworks (MOFs) or covalent organic frameworks (COFs), photocatalysis has remarkably evolved during the last decade. Photocatalytic reticular materials allowed recyclability and easy separation of catalyst from the product, also reaching the activity and selectivity commonly observed for molecular systems. Recently, photocatalytic MOFs and COFs have been applied to synthetic applications in order to obtain organic molecules of different complexity. However, although a good number of works have been devoted to this issue, an updated comprehensive revision on this field is still needed. The aim of this review was to fill this gap covering the following three general aspects: (1) common strategies on the design of reticular photocatalytic materials, (2) a comprehensive discussion of the photocatalytic organic reactions achieved by the use of COFs and MOFs, and (3) some critical considerations highlighting directions that should be considered in order to make advances in the study of photocatalytic COFs and MOFs.

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Sunlight‐Driven Synthesis of 1,2,4‐Thiadiazoles via Oxidative Construction of a Nitrogen‐Sulfur Bond Catalyzed by a Reusable Covalent Organic Framework

Cited by 21 publications

References 62 publications

H₂O₂‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature

H₂O₂‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature

Progress in Development of Photocatalytic Processes for Synthesis of Fuels and Organic Compounds under Outdoor Solar Light

Metal–Organic Frameworks (MOFs) and Covalent Organic Frameworks (COFs) Applied to Photocatalytic Organic Transformations

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Sunlight‐Driven Synthesis of 1,2,4‐Thiadiazoles via Oxidative Construction of a Nitrogen‐Sulfur Bond Catalyzed by a Reusable Covalent Organic Framework

Cited by 21 publications

References 62 publications

H2O2‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature

H2O2‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature

Progress in Development of Photocatalytic Processes for Synthesis of Fuels and Organic Compounds under Outdoor Solar Light

Metal–Organic Frameworks (MOFs) and Covalent Organic Frameworks (COFs) Applied to Photocatalytic Organic Transformations

Contact Info

Product

Resources

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H₂O₂‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature

H₂O₂‐Mediated Synthesis of 1,2,4‐Thiadiazole Derivatives in Ethanol at Room Temperature