Yang Chen, Hui Yan, Hanliang Zheng, Wei-Ping Deng, Zhong Li, Wu-Lin Yang
Herein, we reported an Ir/Brønsted acid dual-catalyzed asymmetric cascade reaction of 2-(1-hydroxyallyl)-phenols with isochroman ketals to produce bisbenzannulated spiroketals in high efficiency with generally high diastereo- and enantioselectivities (up to 17 : 1 dr, >99% ee). The procedure involved the generation of exocyclic enol ethers from isochroman ketals through Brønsted acid catalysis, followed by an Ir-catalyzed enantioselective allylation/spiroketalization sequence with 2-(1-hydroxyallyl)-phenols. Mechanistic investigations and theoretical calculations revealed that chiral iridium catalyst controlled the enantioselectivity, while the high diastereoselectivity was attributed to a Brønsted acid-promoted thermodynamically controlled epimerization process. Furthermore, the asymmetric cascade reaction involving 2-(1-hydroxyallyl)anilines was found to be applicable for synthesizing optically pure bisbenzannulated spiroaminals. Additionally, some of the bisbenzannulated spiroketal products showed promising inhibitory activity against Rhizoctonia solani, suggesting their potential applications in agrochemical discovery.
{"title":"Ir/Brønsted acid dual-catalyzed asymmetric synthesis of bisbenzannulated spiroketals and spiroaminals from isochroman ketals","authors":"Yang Chen, Hui Yan, Hanliang Zheng, Wei-Ping Deng, Zhong Li, Wu-Lin Yang","doi":"10.1039/d4qo01402b","DOIUrl":"https://doi.org/10.1039/d4qo01402b","url":null,"abstract":"Herein, we reported an Ir/Brønsted acid dual-catalyzed asymmetric cascade reaction of 2-(1-hydroxyallyl)-phenols with isochroman ketals to produce bisbenzannulated spiroketals in high efficiency with generally high diastereo- and enantioselectivities (up to 17 : 1 dr, >99% ee). The procedure involved the generation of exocyclic enol ethers from isochroman ketals through Brønsted acid catalysis, followed by an Ir-catalyzed enantioselective allylation/spiroketalization sequence with 2-(1-hydroxyallyl)-phenols. Mechanistic investigations and theoretical calculations revealed that chiral iridium catalyst controlled the enantioselectivity, while the high diastereoselectivity was attributed to a Brønsted acid-promoted thermodynamically controlled epimerization process. Furthermore, the asymmetric cascade reaction involving 2-(1-hydroxyallyl)anilines was found to be applicable for synthesizing optically pure bisbenzannulated spiroaminals. Additionally, some of the bisbenzannulated spiroketal products showed promising inhibitory activity against <em>Rhizoctonia solani</em>, suggesting their potential applications in agrochemical discovery.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142117988","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}
Li-Hua Yang, Lin Chen, Bei Li, Yuan-Xin Jin, Yun Liu, Sha Peng, Long-Yong Xie
The incorporation of phosphorothioate/phosphorodithioate groups into parent molecules has been demonstrated to effectively improve their bioavailability and synthetic application. In this study, we present two types of mild and practical three-component reactions involving cyclic sulfonium salts, S8/Se, H-phosphonates, or cyclic sulfonium salts, P4S10, and alcohols under transition-metal free conditions. This methodology allows for the synthesis of a diverse range of phosphorothioate/phosphorodithioate-containing compounds (93 examples) in satisfactory yields. Preliminary study suggests that the reaction proceeds through a nucleophilic ring-opening process with high atom efficiency.
{"title":"Synthesis of S-alkyl phosphorothioates/phosphorodithioates via ring-opening reaction of sulfonium salts with S8, H-phosphonates or P4S10, and alcohols","authors":"Li-Hua Yang, Lin Chen, Bei Li, Yuan-Xin Jin, Yun Liu, Sha Peng, Long-Yong Xie","doi":"10.1039/d4qo01417k","DOIUrl":"https://doi.org/10.1039/d4qo01417k","url":null,"abstract":"The incorporation of phosphorothioate/phosphorodithioate groups into parent molecules has been demonstrated to effectively improve their bioavailability and synthetic application. In this study, we present two types of mild and practical three-component reactions involving cyclic sulfonium salts, S<small><sub>8</sub></small>/Se, <em>H</em>-phosphonates, or cyclic sulfonium salts, P<small><sub>4</sub></small>S<small><sub>10</sub></small>, and alcohols under transition-metal free conditions. This methodology allows for the synthesis of a diverse range of phosphorothioate/phosphorodithioate-containing compounds (93 examples) in satisfactory yields. Preliminary study suggests that the reaction proceeds through a nucleophilic ring-opening process with high atom efficiency.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118204","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}
Lei Fu, Yang Liu, Zhiyuan Jiang, Zhe Zhang, Qixia Bai, Yu-Qing Li, Zhi Chen, Xiaopeng Li, Pingshan Wang, Tun Wu
Here, we reported the mechanism investigation of anions-induced templation effect, in which nucleophilic anions serving as ligand competitor to destroy partial coordination bonds of the library of metallo-macrocycles and forming quadruple-stranded helicate with vacant cavity. Following the shape and size complementarity, quadruple-stranded helicate can encapsulate spherical halide ions with moderate binding strength and specifical selectivity. Through halophilic templation effect, it is capable of binding and stabilizing bromide within the central cavity of quadruple-stranded helicate and has been exploited to promote C−Br bond cleavage. The dibenzhydryl carbocation (Ph2CH+) generated by the templation effect is an ideal electrophile which can react with various nucleophiles. Therefore, the library can efficiently catalyze a series of organic reactions including hydrolysis, alcoholysis, Ritter reaction and Friedel–Crafts benzylation of arenes and heteroarenes.
{"title":"Selective halide ion binding of templation effect for quadruple stranded-helicate enabling the activation of C-Br bond","authors":"Lei Fu, Yang Liu, Zhiyuan Jiang, Zhe Zhang, Qixia Bai, Yu-Qing Li, Zhi Chen, Xiaopeng Li, Pingshan Wang, Tun Wu","doi":"10.1039/d4qo01373e","DOIUrl":"https://doi.org/10.1039/d4qo01373e","url":null,"abstract":"Here, we reported the mechanism investigation of anions-induced templation effect, in which nucleophilic anions serving as ligand competitor to destroy partial coordination bonds of the library of metallo-macrocycles and forming quadruple-stranded helicate with vacant cavity. Following the shape and size complementarity, quadruple-stranded helicate can encapsulate spherical halide ions with moderate binding strength and specifical selectivity. Through halophilic templation effect, it is capable of binding and stabilizing bromide within the central cavity of quadruple-stranded helicate and has been exploited to promote C−Br bond cleavage. The dibenzhydryl carbocation (Ph2CH+) generated by the templation effect is an ideal electrophile which can react with various nucleophiles. Therefore, the library can efficiently catalyze a series of organic reactions including hydrolysis, alcoholysis, Ritter reaction and Friedel–Crafts benzylation of arenes and heteroarenes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142101829","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}
A family of both axial and planar chiralities in a ferrocene system was synthesized through a Pd-catalyzed domino reaction, yielding remarkable results (up to 76%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >20:1 d.r.). The products were thereafter transformed to ferrocenyl phosphines, featuring all central, planar and axial chiralities, exhibiting excellent diastereoselectivities. Pd-catalyzed enantioselective allylic alkylation reaction demonstrated the potential application of the novel developed ligand, which showcased remarkable enantio-selectivity (99% ee).
{"title":"Enantioselective construction of planar, axially and central chiral ferrocenes phosphine via Pd-catalyzed domino reaction and diastereoselective phosphination","authors":"Congyu Gao, Ting Ren, Yuanyuan Liu, Xiangkun Meng, Junpeng Liu, Zeli Song, Jianfeng Hu, Yong Yang, Wen-Xiong Zhang, Hao Zhang","doi":"10.1039/d4qo01409j","DOIUrl":"https://doi.org/10.1039/d4qo01409j","url":null,"abstract":"A family of both axial and planar chiralities in a ferrocene system was synthesized through a Pd-catalyzed domino reaction, yielding remarkable results (up to 76%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >20:1 d.r.). The products were thereafter transformed to ferrocenyl phosphines, featuring all central, planar and axial chiralities, exhibiting excellent diastereoselectivities. Pd-catalyzed enantioselective allylic alkylation reaction demonstrated the potential application of the novel developed ligand, which showcased remarkable enantio-selectivity (99% ee).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142101866","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}
Siyu Han, Lin Zhao, Xinyu Zhou, Kemeng Zhang, Yunfei Ma, Ge Wu
A metal-free three-component amino- and carbotrideuteromethylthiolation of diverse alkenes in water is developed, providing concise avenues for the preparation of β-functional trideuteromethyl sulfides. Preliminary mechanistic investigations suggest that the single-electron oxidation of CD3SSO3Na by m-CPBA generates a thiyl radical, which initiates the three-component trideuteromethylthiolative difunctionalization of alkenes. Importantly, the excellent functional group tolerance, simple reaction conditions and uniform region-selectivity of the multi-component reaction enable it suitable for the late-stage functionalization of complex molecules.
{"title":"Metal-Free Three-Component Amino- and Carbotrideuteromethylthiolation of Alkenes in Water","authors":"Siyu Han, Lin Zhao, Xinyu Zhou, Kemeng Zhang, Yunfei Ma, Ge Wu","doi":"10.1039/d4qo01081g","DOIUrl":"https://doi.org/10.1039/d4qo01081g","url":null,"abstract":"A metal-free three-component amino- and carbotrideuteromethylthiolation of diverse alkenes in water is developed, providing concise avenues for the preparation of β-functional trideuteromethyl sulfides. Preliminary mechanistic investigations suggest that the single-electron oxidation of CD3SSO3Na by m-CPBA generates a thiyl radical, which initiates the three-component trideuteromethylthiolative difunctionalization of alkenes. Importantly, the excellent functional group tolerance, simple reaction conditions and uniform region-selectivity of the multi-component reaction enable it suitable for the late-stage functionalization of complex molecules.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142101860","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}
Alexander I. Kononov, Sofia O. Strekalova, Vladimir I. Morozov, Konstantin V. Boyko, Vladimir I. Timashev, Michael G. Medvedev, Olga B. Babaeva, Ekaterina V. Kobeleva, Kamil A. Ivshin, Vasily M. Babaev, Yulia H. Budnikova
In this work, we describe a mild electro-oxidative metal-, oxidant- and acid-free direct amidation of aromatic C–H bonds using nitrile solvents as a source of amide and amine moieties. We show that carrying out the reaction in a divided cell makes it possible to eliminate the use of an acid used in previous attempts, enabling at the same time this reaction for easily reducible substrates and paired electrosynthesis. This electrochemical approach was demonstrated on 60 examples of N-phenylamides, including propanil, which has not been obtained under electrochemical conditions so far, and 12 examples of benzoxazoles; it is also amenable to gram-scale synthesis. Mechanistic studies (voltammetry, EPR, and quantum chemical calculations) revealed that the process is initiated by the formation of hydroxyl radicals from residual water molecules on the anode, which attack the nitrile solvent, and the resulting amide radicals add to the arene.
{"title":"Replacing sulfuric acid with water in electrochemical metal-free mild aromatic C–H amidation: a direct route to N-phenylamides","authors":"Alexander I. Kononov, Sofia O. Strekalova, Vladimir I. Morozov, Konstantin V. Boyko, Vladimir I. Timashev, Michael G. Medvedev, Olga B. Babaeva, Ekaterina V. Kobeleva, Kamil A. Ivshin, Vasily M. Babaev, Yulia H. Budnikova","doi":"10.1039/d4qo01296h","DOIUrl":"https://doi.org/10.1039/d4qo01296h","url":null,"abstract":"In this work, we describe a mild electro-oxidative metal-, oxidant- and acid-free direct amidation of aromatic C–H bonds using nitrile solvents as a source of amide and amine moieties. We show that carrying out the reaction in a divided cell makes it possible to eliminate the use of an acid used in previous attempts, enabling at the same time this reaction for easily reducible substrates and paired electrosynthesis. This electrochemical approach was demonstrated on 60 examples of <em>N</em>-phenylamides, including propanil, which has not been obtained under electrochemical conditions so far, and 12 examples of benzoxazoles; it is also amenable to gram-scale synthesis. Mechanistic studies (voltammetry, EPR, and quantum chemical calculations) revealed that the process is initiated by the formation of hydroxyl radicals from residual water molecules on the anode, which attack the nitrile solvent, and the resulting amide radicals add to the arene.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142101863","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}
Aitor Maestro, Sandor B. Otvos, Gerald Auer, C. Oliver Kappe
The development of recyclable catalysts has gained more attention in recent years in order to minimize the environmental effect and the overall cost of catalytic processes. Some of the most broadly used chiral organocatalysts are BINOL-derived chiral phosphoric acids, making it necessary to develop efficient recycling strategies. While literature reports require up to 13 synthetic steps to access recyclable chiral phosphoric acids, here we report a general and concise 9-step approach to anthracene decorated heterogeneous chiral phosphoric acids (PS-Anth), which have shown high performance either in batch or continuous flow without observing catalyst degradation.
{"title":"General and Versatile Synthesis of Highly Recyclable Chiral Phosphoric Acid Organocatalysts","authors":"Aitor Maestro, Sandor B. Otvos, Gerald Auer, C. Oliver Kappe","doi":"10.1039/d4qo01442a","DOIUrl":"https://doi.org/10.1039/d4qo01442a","url":null,"abstract":"The development of recyclable catalysts has gained more attention in recent years in order to minimize the environmental effect and the overall cost of catalytic processes. Some of the most broadly used chiral organocatalysts are BINOL-derived chiral phosphoric acids, making it necessary to develop efficient recycling strategies. While literature reports require up to 13 synthetic steps to access recyclable chiral phosphoric acids, here we report a general and concise 9-step approach to anthracene decorated heterogeneous chiral phosphoric acids (PS-Anth), which have shown high performance either in batch or continuous flow without observing catalyst degradation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142101830","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}
Felix Wech, Niklas Koch, Tizian Müller, Urs Gellrich
Based on the finding that bis(pentafluorophenyl)borane reacts with dienes at elevated temperatures to alkenyl boranes, contrary to the expected alkyl boranes, we developed a scalable and atom-economic bis(pentafluorophenyl)borane-catalyzed process for the synthesis of alkenyl and (homo)allyl boronates from dienes and boronic esters. This method enables the synthesis of cyclic alkenyl boronates with normal ring size that were previously inaccessible via the catalyzed hydroboration of alkynes.
{"title":"Bis(pentafluorophenyl)borane catalyzed atom-economic formation of alkenyl- and (homo)allyl boronates from dienes and boronic esters","authors":"Felix Wech, Niklas Koch, Tizian Müller, Urs Gellrich","doi":"10.1039/d4qo01215a","DOIUrl":"https://doi.org/10.1039/d4qo01215a","url":null,"abstract":"Based on the finding that bis(pentafluorophenyl)borane reacts with dienes at elevated temperatures to alkenyl boranes, contrary to the expected alkyl boranes, we developed a scalable and atom-economic bis(pentafluorophenyl)borane-catalyzed process for the synthesis of alkenyl and (homo)allyl boronates from dienes and boronic esters. This method enables the synthesis of cyclic alkenyl boronates with normal ring size that were previously inaccessible via the catalyzed hydroboration of alkynes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142101865","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}
Chika Yamamoto, Koyo Numata, Minori Suzuki, Suguru Yoshida
A regioselective synthesis of trisubstituted pyridazines from tetrazines and alkynyl sulfides is disclosed. Various pyridazines were selectively prepared by the inverse-electron-demand Diels–Alder reaction and following denitrogenation. Good transformability of sulfur-substituents allowed us to synthesize a range of pyridazines without regioisomers.
{"title":"Regioselective pyridazine synthesis from tetrazines and alkynyl sulfides","authors":"Chika Yamamoto, Koyo Numata, Minori Suzuki, Suguru Yoshida","doi":"10.1039/d4qo01286k","DOIUrl":"https://doi.org/10.1039/d4qo01286k","url":null,"abstract":"A regioselective synthesis of trisubstituted pyridazines from tetrazines and alkynyl sulfides is disclosed. Various pyridazines were selectively prepared by the inverse-electron-demand Diels–Alder reaction and following denitrogenation. Good transformability of sulfur-substituents allowed us to synthesize a range of pyridazines without regioisomers.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142090226","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}
The design and synthesis of novel heteroatom functionalized dienes competent to expand the chemical space of the Diels-Alder cycloaddition reaction to prepare valuable yet challenging architectures continues to be highly desirable in organic synthesis. Here, we present a practical method to synthesize 1,2-dioxygenated dienes via a Pd-catalyzed alkenylation reaction of vinylene carbonate with readily available vinyl triflates. The diene synthesis protocol tolerates various functional groups and substitution types, affording diverse dienes including ones containing natural product fragments. Empowered by the featuring 1,2-carbonated motif, these dienes can smoothly undergo a tandem Diels-Alder cycloaddition/decarboxylative aromatization/oxidation reaction, allowing the concise syntheses of 2-naphthol architectures with ease. In addition, the preparation of substituted phenols as well as natural product derivations are viable employing alkynes as the dienophiles, and excellent regioselectivity are observed when unsymmetrical alkynes were used.
{"title":"Useful 1,2-dioxygenated dienes: syntheses and Diels-Alder reactions en route to substituted 2-naphthols and phenols","authors":"Jiabing Teng, Xifang Zhang, Ying Song, Nayu Chen, Yuanfei Zhang","doi":"10.1039/d4qo01235f","DOIUrl":"https://doi.org/10.1039/d4qo01235f","url":null,"abstract":"The design and synthesis of novel heteroatom functionalized dienes competent to expand the chemical space of the Diels-Alder cycloaddition reaction to prepare valuable yet challenging architectures continues to be highly desirable in organic synthesis. Here, we present a practical method to synthesize 1,2-dioxygenated dienes via a Pd-catalyzed alkenylation reaction of vinylene carbonate with readily available vinyl triflates. The diene synthesis protocol tolerates various functional groups and substitution types, affording diverse dienes including ones containing natural product fragments. Empowered by the featuring 1,2-carbonated motif, these dienes can smoothly undergo a tandem Diels-Alder cycloaddition/decarboxylative aromatization/oxidation reaction, allowing the concise syntheses of 2-naphthol architectures with ease. In addition, the preparation of substituted phenols as well as natural product derivations are viable employing alkynes as the dienophiles, and excellent regioselectivity are observed when unsymmetrical alkynes were used.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142090242","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}
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