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The Difunctionalization of Alkenes Completed by DMTSM and CF3SO2Na without Metal Catalysts DMTSM 和 CF3SO2Na 在不使用金属催化剂的情况下完成的烯烃双官能化反应
IF 2 4区 化学
Synlett Pub Date : 2024-03-22 DOI: 10.1055/a-2283-5928
Siwei Shen, Jinzhao Gao, Xiaofeng Luo, Tianqiang Wang, Peihua Liu, Rulong Yan
{"title":"The Difunctionalization of Alkenes Completed by DMTSM and CF3SO2Na without Metal Catalysts","authors":"Siwei Shen, Jinzhao Gao, Xiaofeng Luo, Tianqiang Wang, Peihua Liu, Rulong Yan","doi":"10.1055/a-2283-5928","DOIUrl":"https://doi.org/10.1055/a-2283-5928","url":null,"abstract":"<p>The electrophilic thiolation of alkenes initiated by DMTSM and the addition of CF<sub>3</sub>SO<sub>2</sub>Na in one pot has been developed. This reaction also can be extended to ArSO<sub>2</sub>Na. This protocol features a good substrate scope, simple procedures, and mild reaction conditions and affords the desired products in moderate yields without metal catalysts.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"144 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199030","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
A Simple Tool to Benchmark Reactivity in Asymmetric Catalysis 不对称催化反应基准的简单工具
IF 2 4区 化学
Synlett Pub Date : 2024-03-21 DOI: 10.1055/s-0042-1751576
Alberto Muñoz, Tomislav Rovis
{"title":"A Simple Tool to Benchmark Reactivity in Asymmetric Catalysis","authors":"Alberto Muñoz, Tomislav Rovis","doi":"10.1055/s-0042-1751576","DOIUrl":"https://doi.org/10.1055/s-0042-1751576","url":null,"abstract":"<p>Herein, we report a simple and noninvasive experimental protocol in which a series of relative reaction rates may be obtained by way of single competition experiments. This approach permits a quantitative comparison of any given number of chiral catalysts relative to a ‘benchmarking’ chiral catalyst – a particularly useful tool since catalyst design and selection have remained largely dependent on chemical intuition. We apply this benchmarking approach towards an asymmetric <i>N</i>-heterocyclic carbene (NHC) catalyzed intramolecular Stetter reaction as a proof-of-concept study. In doing so, we demonstrate a rapid method to assess the complex interplay between catalyst reactivity and stereoelectronic effects – an analytical approach that has heretofore not been attempted for NHCs. To showcase the generality of this method, we apply it to an enantioselective Rh(I)-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and aryl alkynes for a series of chiral phosphoramidite ligands. The results described herein demonstrate that this inexpensive and easily adoptable protocol can reveal complex yet subtle steric and stereoelectronic effects of vastly different chiral catalyst structures, which can further aid with catalyst development and selection for a clearly defined application.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"144 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199211","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Rhodium-Catalyzed Decarbonylative Intramolecular Arylation of 2-(1H-Indole-1-carbonyl)benzoic Acids 铑催化的 2-(1H-吲哚-1-羰基)苯甲酸分子内脱羰基芳基化反应
IF 2 4区 化学
Synlett Pub Date : 2024-03-20 DOI: 10.1055/a-2278-5797
Hirotsugu Suzuki, Yosuke Takemura, Takanori Matsuda
{"title":"Rhodium-Catalyzed Decarbonylative Intramolecular Arylation of 2-(1H-Indole-1-carbonyl)benzoic Acids","authors":"Hirotsugu Suzuki, Yosuke Takemura, Takanori Matsuda","doi":"10.1055/a-2278-5797","DOIUrl":"https://doi.org/10.1055/a-2278-5797","url":null,"abstract":"<p>We developed a redox-neutral synthesis of isoindoloindolone via intramolecular arylation of 2-(1<i>H</i>-indole-1-carbonyl)benzoic acids. This protocol facilitates the formation of various substituted isoindoloindolones in yields ranging from 17% to 80%. Our mechanistic investigations indicate the pivotal role of NaI: the iodide anion promotes the formation of the desired isoindoloindolone, and the sodium cation suppresses the formation of acylated byproducts, thereby enabling the selective formation of isoindoloindolones in acceptable yields.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"1 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199176","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
The Electrochemical trans-Chloroformyloxylation of Unactivated Alkenes 未活化烯烃的电化学反式氯甲酰氧基化反应
IF 2 4区 化学
Synlett Pub Date : 2024-03-20 DOI: 10.1055/s-0043-1763695
Jona Queder, Gerhard Hilt
{"title":"The Electrochemical trans-Chloroformyloxylation of Unactivated Alkenes","authors":"Jona Queder, Gerhard Hilt","doi":"10.1055/s-0043-1763695","DOIUrl":"https://doi.org/10.1055/s-0043-1763695","url":null,"abstract":"<p>An attempted aryl selenium-catalyzed formation of <i>cis</i>-chlorohydrins from alkenes was unsuccessful but led to an electrochemical investigation for the <i>trans</i>-selective chloroformyloxylation of cyclic and acyclic alkenes in moderate to good yields. Interestingly, when 1,1-disubstituted alkenes were used, the corresponding vinyl chloride derivatives were obtained, and the application of 1-phenylcyclohex-1-ene led to the formation of an allyl chloride derivative.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"102 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199224","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Bioorthogonal Chemistry at Radboud University: Past, Present and Future 拉德布德大学的生物正交化学：过去、现在和未来
IF 2 4区 化学
Synlett Pub Date : 2024-03-14 DOI: 10.1055/s-0042-1751569
Floris P. J. T. Rutjes, Kimberly M. Bonger, Kevin Neumann
{"title":"Bioorthogonal Chemistry at Radboud University: Past, Present and Future","authors":"Floris P. J. T. Rutjes, Kimberly M. Bonger, Kevin Neumann","doi":"10.1055/s-0042-1751569","DOIUrl":"https://doi.org/10.1055/s-0042-1751569","url":null,"abstract":"<p>Over the past two decades, bioorthogonal chemistry has profoundly impacted various chemistry-related fields, including chemical biology and drug delivery. This transformative progress stems from collaborative efforts involving chemists and biologists, underscoring the importance of interdisciplinary research. In this Account, we present the developments in bioorthogonal chemistry within our Institute for Molecules and Materials at Radboud University. The chemistry disclosed here spans from strained alkynes and alkenes to drug release and bioconjugation strategies, mirroring the extensive scope provided by bioorthogonal chemistry. By reflecting on the chemistry originating at Radboud University, this Account emphasizes that teamwork is essential for driving significant progress in bioorthogonal chemistry.</p> <p>1 Introduction</p> <p>2 Providing BCN as a Robust Bioorthogonal Tool for Chemical Biology and Beyond</p> <p>3 Towards Readily Available Click-to-Release <i>trans</i>-Cyclooctenes</p> <p>4 Giving Molecules Guidance</p> <p>5 Next Generation of Bioconjugation Strategies: Dynamic Click Chemistry</p> <p>6 Conclusions</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"57 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140152795","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Nickel-Catalyzed Asymmetric Borylative Coupling of 1,3-Dienes with Aldehydes 镍催化的 1,3-二烯与醛的不对称 Borylative 耦合
IF 2 4区 化学
Synlett Pub Date : 2024-03-13 DOI: 10.1055/a-2275-3719
{"title":"Nickel-Catalyzed Asymmetric Borylative Coupling of 1,3-Dienes with Aldehydes","authors":"","doi":"10.1055/a-2275-3719","DOIUrl":"https://doi.org/10.1055/a-2275-3719","url":null,"abstract":"The nickel-catalyzed borylative coupling of aldehydes and 1,3-dienes with diboron reagents offers an efficient method for synthesizing valuable homoallylic alcohols from easily accessible starting materials. However, achieving enantioselectivity in this reaction has been a significant challenge. We discuss our recent report on the first example of a nickel-catalyzed enantioselective borylative coupling of aldehydes with 1,3-dienes, employing a chiral spiro-phosphine–oxazoline ligand. Notably, by utilizing (E)-1,3-dienes or (Z)-1,3-dienes, we can reverse the diastereoselectivity, yielding either anti- or syn-products, respectively.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"16 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140126263","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives 光诱导醚与异氰酸酯的直接氨基甲酰化，以合成 α-酰胺取代的醚衍生物
IF 2 4区 化学
Synlett Pub Date : 2024-03-11 DOI: 10.1055/a-2272-8045
{"title":"Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives","authors":"","doi":"10.1055/a-2272-8045","DOIUrl":"https://doi.org/10.1055/a-2272-8045","url":null,"abstract":"Photoinduced carbamoylation of ethers using isocyanates as amide sources was accomplished under mild and environmentally friendly reaction conditions. A series of isocyanates were tolerated in this protocol to construct α-amide-substituted ether derivatives with desired yields. The method featured broad substrate scope and good functional group tolerance, which could play an important role in the construction of biological molecules with ethers.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"9 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140107121","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Racemosin B and Its Analogues by a Photochemical Cyclization 通过光化学环化法合成消旋肌苷 B 及其类似物
IF 2 4区 化学
Synlett Pub Date : 2024-03-06 DOI: 10.1055/a-2271-7324
Irfan Wazir, Rajagopal Nagarajan
{"title":"Synthesis of Racemosin B and Its Analogues by a Photochemical Cyclization","authors":"Irfan Wazir, Rajagopal Nagarajan","doi":"10.1055/a-2271-7324","DOIUrl":"https://doi.org/10.1055/a-2271-7324","url":null,"abstract":"<p>A simple approach for the synthesis of the alkaloid racemosin B has been developed through a photochemical cyclization reaction with a 33% overall yield without any reagents. This method is sustainable and environmentally friendly because no reagents are required to effect the transformation.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"50 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140056033","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Catalytic Chain Transfer in Crosslinking Photopolymerizations 交联光聚合中的催化链转移
IF 2 4区 化学
Synlett Pub Date : 2024-03-05 DOI: 10.1055/a-2256-2980
{"title":"Catalytic Chain Transfer in Crosslinking Photopolymerizations","authors":"","doi":"10.1055/a-2256-2980","DOIUrl":"https://doi.org/10.1055/a-2256-2980","url":null,"abstract":"Presented here is a detailed account of the development and implementation of macrocyclic cobaloxime complexes as sulfur-free, catalytic chain transfer agents (CTAs) in crosslinking photopolymerizations. Although much of this review is dedicated to understanding the fundamentals of catalytic chain transfer (CCT) in photopolymerizations, its impact on network topology and resultant mechanical properties, future goals of applying this technology to multimaterial 3D printing are also discussed. It is our long-term ambition for catalytic, sulfur-free CTAs to supplant existing consumptive, sulfur-based agents to provide new, unexplored, and not currently possible to fabricate photopolymeric materials with a specific eye towards application in dentistry, additive manufacturing, and responsive materials.1 Introduction2 History of Catalytic Chain Transfer (CCT)3 Understanding Catalyst Purity and Chain Transfer Activity4 Evidencing CCT in a Crosslinking Photopolymerization5 Comparing Cobalt(II)-Catalysts to Other Relevant CTAs6 Performance of Cobalt(II)-Catalysts in Commercial Resins7 Limitations of Approach and Looking Forward","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"9 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140044555","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Fragments Synthesis of A. baumannii ATCC 17961 O-Antigen 鲍曼尼氏菌 ATCC 17961 O 抗原的片段合成
IF 2 4区 化学
Synlett Pub Date : 2024-03-04 DOI: 10.1055/a-2272-8163
Xinxin Li, Liangshen Duan, Deyong Liu, Jianying Qi, Liming Wang, Qingju Zhang
{"title":"Fragments Synthesis of A. baumannii ATCC 17961 O-Antigen","authors":"Xinxin Li, Liangshen Duan, Deyong Liu, Jianying Qi, Liming Wang, Qingju Zhang","doi":"10.1055/a-2272-8163","DOIUrl":"https://doi.org/10.1055/a-2272-8163","url":null,"abstract":"<p>\u0000<i>Acinetobacter baumannii</i> can cause many diseases including septicemia, pneumonia, meningitis, soft tissue, and urinary tract infections. Herein, we described the synthesis of one trisaccharide and two tetrasaccharide fragments derived from <i>A. baumannii</i> ATCC 17961 O-antigen that can be used for screening novel glyco-epitopes and for developing a synthetic carbohydrate-based vaccine against <i>A. baumannii</i> infection. The overall yields for the synthesis of the desired trisaccharide <b>1</b>, tetrasaccharide <b>2</b>, and tetrasaccharide <b>3 </b>are 26.8% (8 steps), 21.6% (9 steps), and 24.5% (6 steps), respectively.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"60 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140034352","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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