Advanced Synthesis & Catalysis最新文献

{"title":"N‐Heterocyclic Carbene‐Catalyzed Enantioselective Synthesis of Spirocyclohexane Oxindoles","authors":"Ye Zhang, Zhoulu Wang, Min Ren, Zhenqian Fu","doi":"10.1002/adsc.202401205","DOIUrl":"https://doi.org/10.1002/adsc.202401205","url":null,"abstract":"A variety of structurally diverse spirocyclohexane oxindoles featuring a quaternary carbon centre have been successfully constructed through an N‐heterocyclic carbene‐catalyzed [4+2] annulation of isatin‐derived enals with α cyano‐β‐methylenones. This domino process exhibits a wide substrate tolerance, operates under mild conditions, and yields products with high enantioselectivity.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832611","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}

{"title":"Synthesis of chiral 2‐trifluoromethyl‐4‐(tetrahydroquinolinyl)‐4H‐chromenes via Pd‐catalyzed asymmetric amination","authors":"Bang Zhong Wang, Luyang Sun, Pengyue Zhang, Shuaibo Zhang, Jinfeng Zhao, Jingping Qu, Yuhan Zhou","doi":"10.1002/adsc.202401422","DOIUrl":"https://doi.org/10.1002/adsc.202401422","url":null,"abstract":"A new strategy for the construction of chiral 4H‐chromene skeleton via Pd‐catalyzed asymmetric amination of 2H‐chromene was reported. A series of chiral 2‐trifluoromethyl‐4H‐chromenes containing 1,2,3,4‐tetrahydroquinoline unit were synthesized in moderate to good yields with excellent enantioselectivity, the method serves as an effective supplement to the construction of chiral 4H‐chromene skeleton.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"144 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832627","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}

{"title":"Visible-Light-Enabled Regioselective C−H alkylation and alkenylation of 2-Aryl Heterocycles using Dual Catalysis","authors":"Rajesh T. Bhawale, Abhinay S. Chillal, Umesh A. Kshirsagar","doi":"10.1002/adsc.202401294","DOIUrl":"https://doi.org/10.1002/adsc.202401294","url":null,"abstract":"<p>Visible light-induced site-selective C−H alkylation and alkenylation of 2-aryl heteroarenes with maleimides at room temperature via dual catalysis in an aqueous medium has been disclosed. This operationally simple and mild approach enables the selective formation of alkylation and alkenylation products up to 92% yield under silver-free conditions with excellent substrate scope. For the mechanistic examination, KIE, H/D labeling experiments, light on-off experiments, and quantum yield measurements were carried out. Moreover, the present approach for the alkylation and alkenylation of 2-aryl heteroarenes is suitable for scalable synthesis.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"30 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841634","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}

{"title":"Diverse Synthesis of Azoles: Construction of ortho‐Azidotetrazoles/Triazoletetrazoles through N‐N Cleavage of 2H‐Indazoles","authors":"Sudip Laru, Suvam Bhattacharjee, Alakananda Hajra","doi":"10.1002/adsc.202401423","DOIUrl":"https://doi.org/10.1002/adsc.202401423","url":null,"abstract":"Herein, we report a conceptually new, general, and efficient approach for the synthesis of valuable ortho‐azido‐1,5‐disubstituted tetrazole and one‐pot synthesis of ortho‐triazoletetrazole derivatives mainly via PIDA mediated N‐N cleavage of the azole ring of 2H‐indazoles using TMSN3. This current methodology represents an array of unsymmetrical ortho‐azidotetrazole and ortho‐triazoletetrazole derivatives with wide functional group tolerance in good to excellent yields under mild reaction conditions. The practical utility of this reaction was showcased through successful scale‐up synthesis and a variety of subsequent derivatizations of ortho‐azidotetrazole products. Mechanistic investigations indicate that the reaction proceeds through a radical pathway.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"47 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832628","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}

{"title":"Photoinduced metal‐free hydrocarboxylation of allylamines","authors":"Dominika Kobus-Bartoszewicz, Mariusz Zalewski, Krzysztof Melcer, Mikołaj Warda, Sebastian Stecko","doi":"10.1002/adsc.202401326","DOIUrl":"https://doi.org/10.1002/adsc.202401326","url":null,"abstract":"Herein, we disclose a new photochemical process to prepare γ‐amino acids from allylamines and formic acid salts. The investigated redox‐neutral hydrocarboxylation process produces high yields across a wide range of functionalized allylamine substrates with excellent regioselectivity. The developed operationally simple protocol can be readily scaled with low photocatalyst loading (from 1% up to 0.02 mol%) without the need for any precautions to exclude air or moisture. The mechanistic working model utilizes a thiol‐catalyzed radical chain process, delivering the hydrogen atom and CO2 from formic acid salt across the alkene substrate through the carboxylate radical (CO2•‐), a crucial reactive intermediate.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"50 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142815791","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}

{"title":"Visible-Light-Induced Acyl and Thiocyano Pyridylation of Alkenes with Aldehyde and NH4SCN","authors":"Xu Wang, Qi-Xuan Jiang, Bi-Yin Xiao, Wei Huang, Feng-Hua Zhang","doi":"10.1002/adsc.202401373","DOIUrl":"https://doi.org/10.1002/adsc.202401373","url":null,"abstract":"β-pyridinyl ketones and β-pyridinyl thiocyanates are commonly used as an essential organic synthesis intermediate and widely present in various drug molecules and bioactive molecules. Herein, a photoredox catalyzed acyl and thiocyano pyridylation of alkenes with aldehydes and NH4SCN via HAT and SET strategy respectively is described. This protocol employs more readily accessible aldehydes and NH4SCN as radical precursors under redox-neutral conditions. Moreover, high atom economy, simple and accessible starting materials, late-stage modification and wide substrate scope including primary, secondary alkyl aldehydes and aromatic aldehydes enable the potential application in the organic synthesis.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142821043","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}

{"title":"Insight into the Key Factors that Influence the Reaction Pathways in the Silyl-Prins Cyclization of gem-Vinylsilyl Alcohols","authors":"Paula González-Andrés, Carlos Diez-Poza, Laura F. Peña, Daniel Gónzalez-Pinardo, Israel Fernandez, Asunción Barbero","doi":"10.1002/adsc.202401437","DOIUrl":"https://doi.org/10.1002/adsc.202401437","url":null,"abstract":"This work provides an in-depth analysis of the factors governing the different reaction pathways in the acid-catalyzed cyclization of gem-vinylsilyl alcohols with aldehydes. The study evaluates the impact of both the ligands attached to silicon and the choice of the Lewis acid on the reaction outcome. Additionally, computational studies offer valuable insights into the mechanism that control these distinct pathways. The process enables the chemo- and stereocontrolled formation of a variety of structural frameworks, offering significant potential for the generation of a broad range of molecular architectures.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"3 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142821044","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}

{"title":"Renewable Platform Chemicals: The Bulk Chemicals of the Future","authors":"Johannes G. de Vries","doi":"10.1002/adsc.202401439","DOIUrl":"https://doi.org/10.1002/adsc.202401439","url":null,"abstract":"&lt;p&gt;\u0000&lt;img alt=\"image\" loading=\"lazy\" src=\"/cms/asset/fcddb95b-8ba2-42f1-9b22-d484c5612bdb/adsc202401439-gra-0001.png\"/&gt;&lt;/p&gt;\u0000&lt;p&gt;Dear friends and colleagues,&lt;/p&gt;\u0000&lt;p&gt;This year, it is 20 years ago that the report, commissioned by the US Department of Energy, “Top Value Added Chemicals from Biomass Volume I–Results of Screening for Potential Candidates from Sugars and Synthesis Gas” was published. Based on the premise that the 21&lt;sup&gt;st&lt;/sup&gt; century will see the use of fossil feedstocks phased out for the production of chemicals, the report analyzed the possibilities of producing chemicals from renewable resources. The authors coined the term &lt;i&gt;platform chemicals&lt;/i&gt; for compounds that not only can be economically produced from biomass, but also are versatile enough to allow conversion into a range of different useful derivatives. The term has caught on, and many chemists agree that renewable platform chemicals will become the bulk chemicals of the future from which a large range of fine chemicals will be prepared.&lt;/p&gt;\u0000&lt;p&gt;In the meantime, large-scale production plants for biomass-based furan compounds have opened in The Netherlands, Canada and the USA. Nevertheless, there is still a long way to go and for this reason a special issue on platform chemicals is a good way to take stock of the current developments in the field.&lt;/p&gt;\u0000&lt;p&gt;It is clear that the past 20 years have seen many new developments in this area. Not only were hundreds of applications found for the existing platform chemicals, but also, a number of new platform chemicals appeared on the stage. One prominent example is 1,3-propanediol, which is produced on large scale in the US by fermentation. In this issue you can read the very first review article on possible applications of 1,3-propanediol.&lt;/p&gt;\u0000&lt;p&gt;Levulinic acid remains an extremely interesting platform chemical in view of all its possible applications. It is currently still produced from furfural, but announcements have been made about a new plant which should produce levulinic acid directly from biomass. This could drastically change the scene. In this issue we have a review article on recent applications of levulinic acid as well as a communication on new syntheses of heterocycles from levulinic acid.&lt;/p&gt;\u0000&lt;p&gt;Chitin is an often-overlooked form of biomass. However, it is abundantly available in the form of shells from crustaceans. In this issue, the syntheses of new heterocyclic compounds made from chitin-derived 3-acetamidofuran are described.&lt;/p&gt;\u0000&lt;p&gt;Dehydration is one of the most essential reactions in biomass conversion and the deoxydehydration reaction is a prime example in which diols are converted to alkenes. In this issue a novel molybdenum-based catalyst for this reaction is revealed.&lt;/p&gt;\u0000&lt;p&gt;Perhaps somewhat unexpected, but biomass-derived chemicals are also finding their way into pharmaceuticals as testified by the review on this topic.&lt;/p&gt;\u0000&lt;p&gt;We hope you enjoy this special issue entitled &lt;i&gt;The Organic Chemistry of Platform","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"62 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810025","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}

{"title":"Developments for Converting Renewables to Platform Chemicals","authors":"Joseph J. Bozell","doi":"10.1002/adsc.202401446","DOIUrl":"https://doi.org/10.1002/adsc.202401446","url":null,"abstract":"&lt;p&gt;\u0000&lt;img alt=\"image\" loading=\"lazy\" src=\"/cms/asset/7c330e0a-5c15-4d9e-a731-2e52804fb67d/adsc202401446-gra-0001.png\"/&gt;&lt;/p&gt;\u0000&lt;p&gt;Terrestrial raw materials, whether petrochemical or renewable, can be converted into small families of building blocks from which other chemicals can be derived. Nonrenewable feedstocks afford a group of olefins, aromatics, CH&lt;sub&gt;4&lt;/sub&gt; or syngas, which serve as &lt;i&gt;platforms&lt;/i&gt; for further conversion into the thousands of products that make up the modern chemical industry.&lt;/p&gt;\u0000&lt;p&gt;The analogous fractionation of renewables provides a ready supply of carbohydrates, lignin or long chain hydrocarbons. However, the polymeric nature and structural complexity of the materials from this fractionation precludes their immediate assignment as platforms. As a result, the challenge becomes determining whether there are small, low molecular weight structures, derived from these biomass fractions, that can be employed in the same manner as the petrochemical industry's olefins and aromatics.&lt;/p&gt;\u0000&lt;p&gt;The concept of using biobased feedstocks for the production of platform chemicals is not new. As a response to the oil crises of the time, efforts were made to define renewable platforms as far back as the mid-1970s and early 1980s.&lt;span&gt;&lt;sup&gt;1-5&lt;/sup&gt;&lt;/span&gt; These initial studies normally focused on “picking winners”, a process of pre-identifying specific, structural targets, frequently hydrocarbon based, against which research should be directed, but sometimes regardless of whether these targets could be reasonably sourced from an initial group of renewable feedstocks.&lt;span&gt;&lt;sup&gt;6, 7&lt;/sup&gt;&lt;/span&gt; It was often observed that transforming highly oxygenated carbohydrates or lignin to petrochemical-like platforms was an economic non-starter.&lt;/p&gt;\u0000&lt;p&gt;Thus, the importance of identifying &lt;i&gt;technology&lt;/i&gt;, rather than structures, tailored to the unique features of biomass became critical to realizing a credible suite of biobased platforms for the chemical industry. What building blocks would be most easily and inexpensively derived from carbohydrates, lignin or plant oils? What processes were needed to make these materials? How can the structural features of biomass be accommodated by the chemical industry? Which of these materials will be true analogs to the petrochemical industry's olefins and aromatics?&lt;/p&gt;\u0000&lt;p&gt;Accordingly, investigations evolved to understand and develop bespoke transformations best suited to provide the interface between renewable feedstocks and the chemical industry. An early US Department of Energy evaluation appeared in 1994, which, while still describing pre-identification of targets, also began to acknowledge the need for technology development.&lt;span&gt;&lt;sup&gt;8&lt;/sup&gt;&lt;/span&gt; With the DOE's release of their “Top Ten” report in 2004, the need for new technology was more strongly established.&lt;span&gt;&lt;sup&gt;9&lt;/sup&gt;&lt;/span&gt; Finally, a highly cited and technology-based revisiting of the Top Ten was published in 2010, providing rationale an","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810026","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}

{"title":"Front Cover Picture: 1,3-Propanediol, an Exemplary Bio-Renewable Organic Platform Chemical (Adv. Synth. Catal. 23/2024)","authors":"Andrew C. Marr","doi":"10.1002/adsc.202401385","DOIUrl":"https://doi.org/10.1002/adsc.202401385","url":null,"abstract":"The front cover, prepared by Ziwei Liu and Zeqing Chen and used with permission, highlights the relationship between massive scale agricultural products and biorenewable organic platform chemicals. Biorenewable organics will enable the synthesis of vital commodities such as medicines when affordable petrochemicals are no longer available. This must be managed carefully to ensure that productivity and benefit to society are maximized, and there is balance between food, water, commodities and the environment. Details on renewable organic platform 1,3-propanediol can be found in the Review by Andrew Marr (A. C. Marr, <i>Adv. Synth. Catal</i>. <b>2024</b>, <i>366</i>, 4569–4579; DOI: 10.1002/adsc.202401066)","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"88 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810021","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}