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Photo-Induced 3-Alkylation of Coumarins with Alkyl halides
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-27 DOI: 10.1002/adsc.202401579
Cheng Yan, Wen-Jiao Zhang, Liu-Yan Qiu, Rui Wang, Weiguo Cao, Zhikun Zhang, Xiao-Jun Tang
{"title":"Photo-Induced 3-Alkylation of Coumarins with Alkyl halides","authors":"Cheng Yan, Wen-Jiao Zhang, Liu-Yan Qiu, Rui Wang, Weiguo Cao, Zhikun Zhang, Xiao-Jun Tang","doi":"10.1002/adsc.202401579","DOIUrl":"https://doi.org/10.1002/adsc.202401579","url":null,"abstract":"A method for the direct 3-alkylation of coumarins utilizing alkyl halides as the alkylating agents has been achieved. This versatile reaction is compatible with a range of alkyl halides, including activated alkyl bromides, perfluoroalkyl iodides, and unactivated alkyl iodides. We propose a mechanism involving photoinduced electron transfer between alkyl halides and coumarins in the first singlet excited (S1) state, which generates alkyl radicals essential for the 3-alkylation process.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"92 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143050525","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Data-Driven Analysis of Ni-Catalyzed Semihydrogenations of Alkynes
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-27 DOI: 10.1002/adsc.202401444
Miguel Martinez-Fernandez, Md Bin Yeamin, David Dalmau, Jorge Carbo, Albert Poater, Juan Vicente Alegre Requena
{"title":"Data-Driven Analysis of Ni-Catalyzed Semihydrogenations of Alkynes","authors":"Miguel Martinez-Fernandez, Md Bin Yeamin, David Dalmau, Jorge Carbo, Albert Poater, Juan Vicente Alegre Requena","doi":"10.1002/adsc.202401444","DOIUrl":"https://doi.org/10.1002/adsc.202401444","url":null,"abstract":"The semihydrogenation of alkynes to alkenes has historically been an essential technique in organic chemistry. In this context, researchers often employ transition metal complexes to achieve this conversion. Given the pronounced polarization of results, often yielding either very high or very low values, it remains challenging to discern the factors influencing reactivity and selectivity in many cases. In this work, we combine different sub-disciplines of digital chemistry with experimental outcomes to rationalize the results of a model Ni-catalyzed semihydrogenation that leads to E-alkenes. First, we analyze the main factors behind successful reactions using a machine learning classification model. The descriptors are computed directly from the SMILES strings of the reacting alkynes using an automated protocol that relies on structural features, molecular mechanics, and semi-empirical techniques. This workflow requires minimal human intervention and provides a fast yet useful approach. Next, we couple the same descriptors with activation barriers calculated with density functional theory, generating a regression model that explains reactivity based on the properties of the alkyne substrates. Overall, this study demonstrates the potential of using a combination of digital chemistry techniques to uncover reaction trends in Ni-catalyzed semihydrogenations of alkynes, an area where human intuition proves limited in application.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143050527","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Electrochemical Oxidative Carbonylation/Coupling Reaction Using Anode to Oxidize the Trasition-Metal-Catalyst and Substrate
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-27 DOI: 10.1002/adsc.202401454
Mengyu Peng, Qingge Zhao, Longqiang Zhao, Huimin Li, Shoucai Wang, Guangbin Jiang, Fanghua Ji
{"title":"Electrochemical Oxidative Carbonylation/Coupling Reaction Using Anode to Oxidize the Trasition-Metal-Catalyst and Substrate","authors":"Mengyu Peng, Qingge Zhao, Longqiang Zhao, Huimin Li, Shoucai Wang, Guangbin Jiang, Fanghua Ji","doi":"10.1002/adsc.202401454","DOIUrl":"https://doi.org/10.1002/adsc.202401454","url":null,"abstract":"We reported an electrochemical oxidative carbonylation of N-phenylpyridin-2-amine derivatives under mild condtions without an external oxidant. Our approach demonstrated a novel electrochemical oxidative carbonylation reaction mode in which the simultaneous reaction of catalyst and substrate with the anode has been developed. Furthermore, an electrochemical C-H activation for the synthesis of cyclized pyridinium ion has also been realized. Mechanistic investigations suggested that the process involved a “PdII/PdIII/PdI/PdII” catalytic cycle, and H2 was generated at the cathode.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"59 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143050530","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible Light-Promoted Cascade Sulfonylation-Cyclization-Aromatization of Tertiary Enamides to Access Multi-substituted Pyridines and 1,2-Dihydropyridines
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-27 DOI: 10.1002/adsc.202401516
Xin-Ming Xu, Jiping Wang, Sen Chen, Xiaoxu Chen, Jinchun Chen, Qian Liu, Zu-Li Wang, Kai Sun, Miao Tian
{"title":"Visible Light-Promoted Cascade Sulfonylation-Cyclization-Aromatization of Tertiary Enamides to Access Multi-substituted Pyridines and 1,2-Dihydropyridines","authors":"Xin-Ming Xu, Jiping Wang, Sen Chen, Xiaoxu Chen, Jinchun Chen, Qian Liu, Zu-Li Wang, Kai Sun, Miao Tian","doi":"10.1002/adsc.202401516","DOIUrl":"https://doi.org/10.1002/adsc.202401516","url":null,"abstract":"Functionalized pyridines and 1,2-dihydropyridines are crucial organic entities in natural products, organic materials, drugs and catalysts. Despite progress, a facile and eco-friendly synthesis remains desirable so far. In this context, we disclose a novel visible light-promoted radical cascade sulfonylation-cyclization-aromatization of N-propargyl enamides with selenosulfonates. This approach avoids the use of metal- or photocatalyst, bases and external oxidants, marking a significant advance in sustainable and green chemistry accords. Utilizing this protocol, we successfully synthesized a diverse range of sulfonated 1,2-dihydropyridines and pyridines, featuring good functional group compatibility, simple operation and mild condition.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"50 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143050528","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Combined Electrooxidation and Proline Catalysis for Asymmetric Formal Cross-Dehydrogenative Coupling of Benzylic Alcohols with Ketones
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-27 DOI: 10.1002/adsc.202401466
Hong-Ping Pu, Chao-Jiu Long, Zhe-Kai Liu, Zhi Guan, Yan-Hong He
{"title":"Combined Electrooxidation and Proline Catalysis for Asymmetric Formal Cross-Dehydrogenative Coupling of Benzylic Alcohols with Ketones","authors":"Hong-Ping Pu, Chao-Jiu Long, Zhe-Kai Liu, Zhi Guan, Yan-Hong He","doi":"10.1002/adsc.202401466","DOIUrl":"https://doi.org/10.1002/adsc.202401466","url":null,"abstract":"This article presents a method for asymmetric formal cross-dehydrogenative coupling of benzylic alcohols with ketones through combined electrooxidation and organocatalysis. Employing inexpensive and environmentally friendly proline as a chiral organocatalyst, various benzylic alcohols and simple ketones serve as substrates to directly obtain diverse chiral β-hydroxycarbonyl compounds with moderate to good yields (up to 85%) and excellent stereoselectivity (up to 99% ee and 99:1 dr). The reaction proceeds under mild conditions at room temperature in air, without oxidants or additives, demonstrating robust functional group tolerance and atom efficiency. Hydrogen gas released at the cathode is the sole byproduct. Using L- or D-proline allows straightforward access to both chiral configurations of β-hydroxycarbonyl compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"35 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143050531","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Magnesium-Mediated Reductive Defluorinative Cross-Electrophile Coupling of α-Trifluoromethyl Styrenes with CO2 and Acyl Imidazoles
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-27 DOI: 10.1002/adsc.202401594
Jianjun Hao, Lu Ren, Jingwen Tan, Yulin Peng, Lin-Hai Jing, Pan Han
{"title":"Magnesium-Mediated Reductive Defluorinative Cross-Electrophile Coupling of α-Trifluoromethyl Styrenes with CO2 and Acyl Imidazoles","authors":"Jianjun Hao, Lu Ren, Jingwen Tan, Yulin Peng, Lin-Hai Jing, Pan Han","doi":"10.1002/adsc.202401594","DOIUrl":"https://doi.org/10.1002/adsc.202401594","url":null,"abstract":"Gem-difluoroethylene moiety holds pivotal roles in drug research owing to its unique ability as a bioisostere of the carbonyl group. Here, magnesium-mediated reductive defluorinative cross-electrophile coupling of α-trifluoromethyl styrene with carbon-centered electrophiles was developed. This method featured readily accessible reagents, mild conditions, and wide substrate scope, enabling the efficient production of gem-difluoroallyl carboxylic acid and ketones. The establishment of this protocol will offer a general alternative for the acquisition of gem-difluoroethylene compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"47 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143050526","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Layered Copper-based 2D-MOFs for Enhanced Catalytic Regioselective Phosphorylation of Alkynes and P-H Bonds
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-24 DOI: 10.1002/adsc.202401414
Shipan Xu, Biquan Xiong, Minjing Yuan, Weifeng Xu, Renfeng Cao, Fan Cao, Longzhi Zhu, Shuang-Feng Yin
{"title":"Synthesis of Layered Copper-based 2D-MOFs for Enhanced Catalytic Regioselective Phosphorylation of Alkynes and P-H Bonds","authors":"Shipan Xu, Biquan Xiong, Minjing Yuan, Weifeng Xu, Renfeng Cao, Fan Cao, Longzhi Zhu, Shuang-Feng Yin","doi":"10.1002/adsc.202401414","DOIUrl":"https://doi.org/10.1002/adsc.202401414","url":null,"abstract":"A functionalized heterogeneous Cu-based metal-organic framework (Cu-2D-MOF) was synthesized through the reaction of Cu(NO3)2·3H2O with 2,3,5,6-tetrafluoroterephthalic acid and 4,4'-bipyridine. The synthesized material underwent comprehensive characterization using various techniques, including FT-IR spectroscopy, N2 physical adsorption, scanning electron microscopy (SEM), and X-ray photoelectron spectroscopy (XPS). Subsequently, the catalytic performance of Cu-2D-MOFs was assessed in the hydrophosphorylation and aerobic oxidative dehydrogenative coupling reactions involving alkynes and P-H bonds. The catalyst demonstrated remarkable catalytic activity in both transformations, effectively yielding a wide variety of (E)-alkenyl-phosphoryl and alkynyl-phosphoryl compounds, respectively. Notably, the incorporation of this MOF material facilitated the phosphorylation reaction to proceed seamlessly, eliminating the necessity for supplementary small molecular organic ligands. Furthermore, the catalyst demonstrated ease of recovery and recyclability through a simple recovery process. Employing a systematic approach of sequential control experiments, we have delineated the potential transformation pathway of the reaction and consequently hypothesized a probable reaction mechanism for the observed transformation.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"87 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143031276","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Front Cover Picture: (Adv. Synth. Catal. 2/2025)
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-24 DOI: 10.1002/adsc.202580201
{"title":"Front Cover Picture: (Adv. Synth. Catal. 2/2025)","authors":"","doi":"10.1002/adsc.202580201","DOIUrl":"https://doi.org/10.1002/adsc.202580201","url":null,"abstract":"As of 2025, Advanced Synthesis and Catalysis joins the Advanced Portfolio from Wiley. Led by the world-renowned journal Advanced Materials, the Advanced Portfolio is a family of globally respected, high-impact journals that disseminate the best science. With the inclusion of Advanced Synthesis and Catalysis, it is broadening its reach into the field of chemistry. Cover image provided courtesy of Liang Zhao and co-workers from Dalian University of Technology.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027014","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Alkylation of Imines with Alkyl Halides under Electrochemical Conditions 电化学条件下亚胺与卤代烃的烷基化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-22 DOI: 10.1002/adsc.202401527
Tan Zhang, Mengyun Wu, Wenhui Wang, Yingsibing Fan, Ping Liu, Peipei Sun
{"title":"Alkylation of Imines with Alkyl Halides under Electrochemical Conditions","authors":"Tan Zhang, Mengyun Wu, Wenhui Wang, Yingsibing Fan, Ping Liu, Peipei Sun","doi":"10.1002/adsc.202401527","DOIUrl":"https://doi.org/10.1002/adsc.202401527","url":null,"abstract":"An electrochemical protocol for the alkylation of imines was developed by using easily available alkyl halides as the alkyl sources, graphite felt (GF) as anode and zinc plate as cathode. Various substituted imines, alkyl bromides and alkyl iodides were suitable for this reaction and a series of α‐branched amines were obtained in moderate to good yields. This method provides a green way for the addition of imines to avoid the need for metal reagents, chemical oxidants and reductants, which makes it has a good application prospect in drug synthesis.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"11 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142992471","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Corrigendum Letter for Adv. Synth. Catal. 2013, 355, 308 – 314 adh . Synth的勘误信。植物学报，2013,35 (5):308 - 314
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-01-22 DOI: 10.1002/adsc.202500046
Hao Zhu
{"title":"Corrigendum Letter for Adv. Synth. Catal. 2013, 355, 308 – 314","authors":"Hao Zhu","doi":"10.1002/adsc.202500046","DOIUrl":"https://doi.org/10.1002/adsc.202500046","url":null,"abstract":"I am writing to you regarding the correction of our published article entitled “Heterogeneous Bifunctional Catalytic, Chemo‐, Regio‐ and Enantioselective Cascade Inverse Electron Demand Diels–Alder Reaction, Adv. Synth. Catal. 2013, 355, 308 – 314.” Recently, after someone's reminder and our careful review, we found that there are some errors in the annotation of Figure 1 in the article. Therefore, it is necessary to contact you for correction. Please refer to the attachment for detailed information. We apologize for any inconvenience these errors may have caused and assure you that they were unintentional. These errors in expression do not undermine the authenticity of the original research findings or the main conclusions of this article. We kindly request your confirmation and acknowledgment of these amendments by signing and returning a copy of this corrigendum letter. Once the necessary corrections are made and agreed upon, we will consider the original document amended accordingly.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"10 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142992686","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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