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Enantioselective Synthesis of α-Chiral Sulfonates through Palladium-Catalyzed Tsuji-Trost Sulfonylation with Sulfur Dioxide
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo01887g
Xiaochun He, Fei Zhou, Qingqing Wang, Xiaohong Wang, Zhiqian Chang, Xuemei Zhang, Zhong Lian
{"title":"Enantioselective Synthesis of α-Chiral Sulfonates through Palladium-Catalyzed Tsuji-Trost Sulfonylation with Sulfur Dioxide","authors":"Xiaochun He, Fei Zhou, Qingqing Wang, Xiaohong Wang, Zhiqian Chang, Xuemei Zhang, Zhong Lian","doi":"10.1039/d4qo01887g","DOIUrl":"https://doi.org/10.1039/d4qo01887g","url":null,"abstract":"α-Chiral sulfonates have remained largely uncharted territory, primarily due to the intrinsic difficulties associated with achieving stereocontrol. In this study, we present an innovative three-component palladium-catalyzed asymmetric Tsuji-Trost sulfonylation protocol, which introduces a novel strategy for the synthesis of enantiomerically enriched α-chiral sulfonates, utilizing S(VI) complexes as intermediates. This method is versatile, applicable to a diverse array of allylic acetates and alcohols, thereby allowing for the efficient synthesis of α-chiral sulfonates with high yields, exceptional regio- and enantioselectivities (up to 99% ee). In conclusion, this strategy offers a practical and efficient route for the generation of chiral α-substituted linear allylic sulfonates.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"271 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Biological Studies of 3-Trideuteromethylated Chromones and their Heteroatom Analogues
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo02081b
Kaiyue Yang, Dongke Zhang, Ce Yang, Xueyan Yang, Jiaxin He, Haofeng Shi, Zichuan Liu, Yunfei Du
{"title":"Synthesis of Biological Studies of 3-Trideuteromethylated Chromones and their Heteroatom Analogues","authors":"Kaiyue Yang, Dongke Zhang, Ce Yang, Xueyan Yang, Jiaxin He, Haofeng Shi, Zichuan Liu, Yunfei Du","doi":"10.1039/d4qo02081b","DOIUrl":"https://doi.org/10.1039/d4qo02081b","url":null,"abstract":"The bioactive trideuteromethylated chromones and their heteroatom analogues were synthesized via trideuteromethylation of chromones and their heteroatom analogues by utilizing Fenton's reagent system with d6-DMSO as the “CD3” source. Mechanistically, it was postulated that the hydroxyl radical generated from Fenton's reagent system first reacted with d6-DMSO to give the electrophilic trideuteromethyl radical, which underwent radical substitution with chromones and their heteroatom analogues to give the title products. The obtained trideuteromethylated compounds were subjected to biological studies and the results revealed that this class of trideuteromethylated chromones and their heteroatom analogues exhibit good to excellent in vitro anti-lung carcinoma and anti-hepatoma activities.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841637","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo02118e
Jiuling Li, Xinyu Jia, Qiangguo Yang, Jiakang Guo, Qianhui Ren, Taichen Liu, Kai Wei, Zheng-Hui Kang
{"title":"Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions","authors":"Jiuling Li, Xinyu Jia, Qiangguo Yang, Jiakang Guo, Qianhui Ren, Taichen Liu, Kai Wei, Zheng-Hui Kang","doi":"10.1039/d4qo02118e","DOIUrl":"https://doi.org/10.1039/d4qo02118e","url":null,"abstract":"An environmental-friendly and safe method has been developed to synthesize 1,5-disubstituted 1,2,3-triazoles containing difluoromethyl fragments, which can be obtained from readily available 2,2-difluoroarylethylamines under azide-free conditions. The classic conversion mode of acetic acid with tert-butyl nitrite is the critical factor in the reaction, allowing the diazo species in-situ generated to immediately react with the raw materials to give the desired products in good yields. The mild reaction conditions and convenient operations not only indicate such approach providing an attractive alternative method for the synthesis of polysubstituted 1,2,3-triazoles, but also further promote the applications of 2,2-difluoroarylethylamines in organic synthesis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"69 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841639","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2: synthesis of 2-aminoethyl dithiocarbamates
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-18 DOI: 10.1039/d4qo02148g
Wenxue Li, Xueying Yang, Man Miao, Fengkai Sun, Hui Yuan, Xiaobing Lan, Jianqiang Yu, Jian Zhang, Zhenyu An
{"title":"Solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2: synthesis of 2-aminoethyl dithiocarbamates","authors":"Wenxue Li, Xueying Yang, Man Miao, Fengkai Sun, Hui Yuan, Xiaobing Lan, Jianqiang Yu, Jian Zhang, Zhenyu An","doi":"10.1039/d4qo02148g","DOIUrl":"https://doi.org/10.1039/d4qo02148g","url":null,"abstract":"This study presents a solvent-controlled C2/C3-regioselective ring-opening/coupling of aziridines with amines and CS2, yielding two distinct types of 2-aminoethyl dithiocarbamates without the need for additives or non-green activation strategy. Featuring excellent atom economy, low-cost starting materials, broad substrate scope, and compatibility with clinically relevant molecules, this reaction is both efficient and sustainable for practical application. Control experiments and DFT calculations reveal that hydrogen bonding between solvents and aziridines directs selectivity by modulating orbital distributions, clarifying the selective reaction pathways.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841643","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Cyclic Phosphonium-Borate Compounds through Reaction of Benzynes and Frustrated Lewis Pairs 通过苄基与受挫路易斯对的反应合成环状膦硼酸盐化合物
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01852d
Pei Xie, Fang Zhang, Zhihua Cai, Yating Zheng, Leifang Wu, Lin He
{"title":"Synthesis of Cyclic Phosphonium-Borate Compounds through Reaction of Benzynes and Frustrated Lewis Pairs","authors":"Pei Xie, Fang Zhang, Zhihua Cai, Yating Zheng, Leifang Wu, Lin He","doi":"10.1039/d4qo01852d","DOIUrl":"https://doi.org/10.1039/d4qo01852d","url":null,"abstract":"A practical method for the construction of stable zwitterionic phosphonium-borate compounds via trapping of benzynes by phosphine-borane frustrated Lewis pairs have been developed. A series of structurally diverse phosphonium-borate inner salts were thus prepared in moderate to good yields under mild reaction conditions. DFT calculations were also conducted to support a possible pathway of this reaction.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","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":"142832168","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Ag(I)-linked Bis-calix[4]pyrrole Molecular Capsule and its Selective Recognition of Fluoride Anion Ag(I)-linked Bis-calix[4]pyrrole 分子胶囊及其对氟阴离子的选择性识别
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo02177k
Xiaolong Chen, Zhiye Zheng, Shunfeng Peng, Ying Guo, Ying Gao, Chenxing Guo, Jonathan L. Sessler, Hong-Yu Wang
{"title":"Ag(I)-linked Bis-calix[4]pyrrole Molecular Capsule and its Selective Recognition of Fluoride Anion","authors":"Xiaolong Chen, Zhiye Zheng, Shunfeng Peng, Ying Guo, Ying Gao, Chenxing Guo, Jonathan L. Sessler, Hong-Yu Wang","doi":"10.1039/d4qo02177k","DOIUrl":"https://doi.org/10.1039/d4qo02177k","url":null,"abstract":"A well-defined “four-wall” capsule (3) was constructed based on the coordination-driven self-assembly of a tetratopic pyridine-functionalized calix[4]pyrrole cavitand with four stabilizing pyridine···Ag+···pyridine coordination bonds in N,N-dimethylformamide (DMF). Capsule was 3 characterized by means of various techniques, including 1H nuclear magnetic resonance (NMR) spectroscopy, diffusion ordered NMR spectroscopy (DOSY), electrospray ionization mass spectrometry (ESI-MS), and single crystal X-ray diffraction analyses. The tetra-α-meso-pyridyl extended calix[4]pyrrole ligand 2 and the corresponding dimeric capsule 3 were found to recognize selectively the fluoride anion over other halide anions (chloride, bromide, and iodide anions) in DMF. Cavitand 2 was found to bind and release Ag+ via a fast equilibrium exchange process on the NMR timescale, whereas the fluoride binding of both 2 and capsule 3 proved slow on the NMR timescale. The transformation among multiple molecular states, viz. monomeric form 2, capsule 3, and their corresponding fluoride-bound complexes F−⊂2 and 2F−⊂3, could be modulated by the addition of silver, fluoride, and chloride ions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"40 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832167","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
In situ generated aza-π-allylpalladium zwitterions as nucleophilic triggers for enantioselective [4 + 2] cycloaddition with electron-deficient alkenes toward functionalized chiral piperidines 原位生成的杂氮-π-烯丙基钯齐聚物作为亲核触发器，与缺电子烯进行对映选择性[4 + 2]环加成，生成功能化手性哌啶
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo02058h
Han-Yang Zhong, Hong-Wei Xiao, Ji-Hong Liu, Zhen-Zhen Ge, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan
{"title":"In situ generated aza-π-allylpalladium zwitterions as nucleophilic triggers for enantioselective [4 + 2] cycloaddition with electron-deficient alkenes toward functionalized chiral piperidines","authors":"Han-Yang Zhong, Hong-Wei Xiao, Ji-Hong Liu, Zhen-Zhen Ge, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan","doi":"10.1039/d4qo02058h","DOIUrl":"https://doi.org/10.1039/d4qo02058h","url":null,"abstract":"Aza-π-allylpalladium zwitterions, in situ generated from Pd-catalyzed decarboxylation of methylene cyclic carbamates, have so far been reported only as electrophilic triggers for promoting various asymmetric reactions. Herein, for the first time, these zwitterions are used as nucleophilic triggers for the enantioselective [4+2] cycloaddition with electron-deficient alkenes. This reaction provides a facile method to access structurally diverse chiral piperidine derivatives in good yields and enantioselectivities. The utility of this method was demonstrated by a large-scale reaction and product derivatizations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"18 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832169","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Pyrrolo[1,2-a]quinoxalines via an Electrochemical C(sp3)-H Functionalization
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01981d
Sijie Peng, Tong Li, Kai Li, Qi Sun, Zhiyong Wang
{"title":"Synthesis of Pyrrolo[1,2-a]quinoxalines via an Electrochemical C(sp3)-H Functionalization","authors":"Sijie Peng, Tong Li, Kai Li, Qi Sun, Zhiyong Wang","doi":"10.1039/d4qo01981d","DOIUrl":"https://doi.org/10.1039/d4qo01981d","url":null,"abstract":"An efficient iodine-mediated electrochemical C(sp3)-H cyclization was developed under mild conditions. A variety of functionalized quinoxalines can be obtained with good to excellent yields by virtue of this method. The reaction features a broad substrate scope, the regulation of product distribution, scalable preparation and high atomic economy. The reaction mechanism was investigated in detail.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841647","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Recent advances of calcium(II) triflimide in organic synthesis 三亚甲基钙（II）在有机合成中的最新进展
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo02164a
Haoran Li, Minyao Kuang, Yuwei Liu, Wei Yi, Shengdong Wang
{"title":"Recent advances of calcium(II) triflimide in organic synthesis","authors":"Haoran Li, Minyao Kuang, Yuwei Liu, Wei Yi, Shengdong Wang","doi":"10.1039/d4qo02164a","DOIUrl":"https://doi.org/10.1039/d4qo02164a","url":null,"abstract":"Environmentally benign calcium(II) triflimide has emerged as a sustainable substitute for transition-metal catalysts, rare-earth metals, and strong Brønsted acids in promoting organic synthesis, thereby attracting considerable attention. Recently, elegant methodologies involving calcium(II) triflimide have been developed, such as cyclizations, dehydrative functionalizations, hydroarylation reactions, hydrofunctionalizations, reductions, rearrangements, and novel selenylations, hese have been applied to a diverse range of substrates inculding alcohols, alkenes, alkynes, carbonyl compounds, imines, N,O-acetals, and selenides for the formation of C–C or C–X bond. This review provides a comprehensive and detailed overview of the recent progress in the application of calcium(II) triflimideas as an organic synthesis catalyst, summarizing the crucial achievements in reaction methodologies and the plausible reaction mechanisms.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"11 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832170","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Tandem Synthesis of Enantioenriched Spirolactones via One-Pot Heck-Matsuda Reactions Directly from Nitroarenes 通过一锅 Heck-Matsuda 反应直接从硝基烯烃串联合成对映体丰富的螺内酯
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2024-12-17 DOI: 10.1039/d4qo01979b
Tomaz Chorro, Clemens Kaussler, Julia V. Kolodiazhnaia, Frank Jensen, Troels Skrydstrup, Carlos Roque Correia
{"title":"Tandem Synthesis of Enantioenriched Spirolactones via One-Pot Heck-Matsuda Reactions Directly from Nitroarenes","authors":"Tomaz Chorro, Clemens Kaussler, Julia V. Kolodiazhnaia, Frank Jensen, Troels Skrydstrup, Carlos Roque Correia","doi":"10.1039/d4qo01979b","DOIUrl":"https://doi.org/10.1039/d4qo01979b","url":null,"abstract":"We report herein a novel, efficient, and expeditious approach for enantioselective intramolecular carbonylative Heck-Matsuda reaction, employing highly accessible, stable, and cost-effective nitroarenes as masked electrophiles. This tandem process combines the one-pot reduction of nitroarenes to the respective anilines, diazotization, Heck-Matsuda, carbonylation, and cyclization, enabling the synthesis of enantioenriched spirolactones. The method achieves overall yields of up to 76% with excellent enantiomeric ratios of up to 96:4 under mild conditions. Isotopically labeled products are readily obtained with near stoichiometric 13C carbon monoxide. Importantly, nitroarenes are used as masked electrophiles, which serve as an advantageous alternative to anilines and aryldiazonium salts for the Heck-Matsuda reaction. This approach thereby avoids the isolation of sensitive aryldiazonium salt intermediates and, consequently, the dangers associated with them. Density Functional Theory (DFT) calculations provide precise insights into the enantioenrichment mechanism, highlighting the significance of Pd carbonyl complexes for efficient diastereoconvergence. Microkinetic modeling of the computationally obtained reaction network results in an enantioenrichment of sub-kcal-accuracy in comparison to the experiment. This work not only showcases the level of complexity achievable in the field of tandem reactions but also highlights the utility of nitroarenes in complex organic transformations, demonstrating their potential for both academic and industrial applications.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832217","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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