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Latest Developments in Palladium and Nickel-Catalyzed Cross-Couplings for Aryl Chlorides: Suzuki-Miyaura and Buchwald-Hartwig Reactions 钯和镍催化的芳基氯化物交叉耦合反应的最新进展：Suzuki-Miyaura和Buchwald-Hartwig反应
Synthesis Pub Date : 2024-06-13 DOI: 10.1055/a-2344-5677
Abhiji Sen, Yoichi Yamada
{"title":"Latest Developments in Palladium and Nickel-Catalyzed Cross-Couplings for Aryl Chlorides: Suzuki-Miyaura and Buchwald-Hartwig Reactions","authors":"Abhiji Sen, Yoichi Yamada","doi":"10.1055/a-2344-5677","DOIUrl":"https://doi.org/10.1055/a-2344-5677","url":null,"abstract":"Palladium- and nickel-catalyzed cross-couplings are powerful methods for constructing C-C and C-N bonds, particularly through Suzuki-Miyaura and Buchwald-Hartwig reactions. Although aryl iodides, bromides, and triflates are the most commonly used substrates, aryl chlorides are less frequently utilized due to their lower reactivity. However, they are appealing because they are readily available and inexpensive. This short review highlights recent developments in Suzuki-Miyaura and Buchwald-Hartwig cross-couplings of aryl chlorides, using both homogeneous and heterogeneous catalysis with palladium and nickel.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141345424","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Rapid and Mild Nucleophilic Substitution of a Highly Active (Indol-2-yl)methyl Electrophile in a Microflow Reactor 在微流反应器中快速温和地亲核取代高活性（吲哚-2-基）甲基亲电子体
Synthesis Pub Date : 2024-06-13 DOI: 10.1055/s-0043-1775370
Shinichiro Fuse, Yuma Matsuura, Naoto Yamasaki
{"title":"Rapid and Mild Nucleophilic Substitution of a Highly Active (Indol-2-yl)methyl Electrophile in a Microflow Reactor","authors":"Shinichiro Fuse, Yuma Matsuura, Naoto Yamasaki","doi":"10.1055/s-0043-1775370","DOIUrl":"https://doi.org/10.1055/s-0043-1775370","url":null,"abstract":"<p>Indoles are common motifs in functional agricultural and pharmaceutical molecules. Heteroatom alkylation is the most frequently used chemical reaction in the pharmaceutical field. Developing protocols for the nucleophilic substitution of (indol-2-yl)methyl electrophiles is important for functionalizing indoles. There are few studies on the nucleophilic substitution at the 2′-position of the electrophiles without an electron-withdrawing group at the 1-position or substituents at the 2′- and 3-positions, where the existing approaches require high temperatures and long reaction times. In this study, we demonstrated rapid (7–12 s) and mild (25 °C) microflow nucleophilic substitution at the 2′-position of indole derivatives without an electron-withdrawing group at the 1-position and substituents at the 2′- or 3-positions. Comparable batch conditions resulted in a lower yield.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528660","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Metal-Free Synthesis of Selanyl-Substituted Chromenones via Selanylation­/Cyclization of Alkynyl Aryl Ketones 通过炔基芳基酮的硒化/环化无金属合成硒基取代的色酮
Synthesis Pub Date : 2024-06-12 DOI: 10.1055/s-0043-1775369
Xi-Rui Gong, Yi-Huan Zhou, Mei-Lin Ren, Yan-Yan Chen, Yan-Li Xu
{"title":"Metal-Free Synthesis of Selanyl-Substituted Chromenones via Selanylation­/Cyclization of Alkynyl Aryl Ketones","authors":"Xi-Rui Gong, Yi-Huan Zhou, Mei-Lin Ren, Yan-Yan Chen, Yan-Li Xu","doi":"10.1055/s-0043-1775369","DOIUrl":"https://doi.org/10.1055/s-0043-1775369","url":null,"abstract":"<p>A variety of 2-substituted 3-selanyl-chromenones are readily prepared through a cascade selanylation/cyclization of alkynyl aryl ketones with sulfonoselenoates. This transformation is performed under metal-free conditions and does not require an additional oxidant. It also has the advantage of broad functional group tolerance and scalability.</p>","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528662","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Design, Synthesis, and Assessment of Tricarboxylic Acid Cycle Probes 三羧酸循环探针的设计、合成和评估
Synthesis Pub Date : 2024-06-12 DOI: 10.1055/a-2335-8736
Joseph Chen, Darrian Chao, Uyen Phuong Tran, Kelvin L. Billingsley
{"title":"Design, Synthesis, and Assessment of Tricarboxylic Acid Cycle Probes","authors":"Joseph Chen, Darrian Chao, Uyen Phuong Tran, Kelvin L. Billingsley","doi":"10.1055/a-2335-8736","DOIUrl":"https://doi.org/10.1055/a-2335-8736","url":null,"abstract":"<p>Hyperpolarized <sup>13</sup>C magnetic resonance spectroscopy can provide unique insights into metabolic activity <i>in vivo</i>. Despite the advantages of this technology, certain metabolic pathways such as the tricarboxylic acid (TCA) cycle are more challenging to examine due to the limitations associated with currently available hyperpolarized <sup>13</sup>C probes. In this report, we systematically employ computational analyses, synthetic techniques, and <i>in vitro</i> studies to facilitate the design of new chemical probes for the TCA cycle. This platform allows for the rapid identification of probe scaffolds that are amenable to hyperpolarized <sup>13</sup>C experimentation. Using these results, we have developed two <sup>13</sup>C-labeled chemical probes, [1,4-<sup>13</sup>C<sub>2</sub>]-dipropyl succinate and [1,4-<sup>13</sup>C<sub>2</sub>]-diallyl succinate, which are employed in hyperpolarized <sup>13</sup>C metabolic studies.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528663","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
SYNFORM ISSUE 2024/7 同步信息》第 2024/7 期
Synthesis Pub Date : 2024-06-12 DOI: 10.1055/s-0043-1763989
M. Zanda
{"title":"SYNFORM ISSUE 2024/7","authors":"M. Zanda","doi":"10.1055/s-0043-1763989","DOIUrl":"https://doi.org/10.1055/s-0043-1763989","url":null,"abstract":"","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141354755","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Efficient Synthesis of Esters by Cleavage of C–S and C–N Bonds via Alkylation and Activation of Thioamides 通过硫代酰胺的烷基化和活化作用裂解 C-S 和 C-N 键从而高效合成酯类化合物
Synthesis Pub Date : 2024-06-11 DOI: 10.1055/s-0043-1774910
Jigarkumar K. Vankar, Jaydeepbhai P. Jadav, Guddeangadi N. Gururaja
{"title":"Efficient Synthesis of Esters by Cleavage of C–S and C–N Bonds via Alkylation and Activation of Thioamides","authors":"Jigarkumar K. Vankar, Jaydeepbhai P. Jadav, Guddeangadi N. Gururaja","doi":"10.1055/s-0043-1774910","DOIUrl":"https://doi.org/10.1055/s-0043-1774910","url":null,"abstract":"<p>A mild and efficient reaction for synthesizing esters from thioamide precursors has been established. This method is accomplished in one pot under mild conditions. The process involves the alkylation and activation of inert thioamides, which leads to the cleavage of stable C–N and C–S bonds, eventually resulting in valuable esters with a broad range of substrates. The transformation can be easily carried out at room temperature using thioamide substrates, reactants, and activating agents. This protocol has been demonstrated by synthesizing important esters with applications.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141501755","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
RhI-Catalysed Cycloisomerization Reactions of 1,7-Enynes to Access Cage-like Tricyclo[3.2.2.06,8]nonenes RhI 催化的 1,7-炔烃环异构化反应生成笼状三环[3.2.2.06,8]壬烯
Synthesis Pub Date : 2024-06-11 DOI: 10.1055/a-2343-0881
Jinbao Fan, Liyang Shi, Qing Wang, Yan Zeng, Wei Cao, Guangyao Zeng, Yingjun Zhou, Xu Deng
{"title":"RhI-Catalysed Cycloisomerization Reactions of 1,7-Enynes to Access Cage-like Tricyclo[3.2.2.06,8]nonenes","authors":"Jinbao Fan, Liyang Shi, Qing Wang, Yan Zeng, Wei Cao, Guangyao Zeng, Yingjun Zhou, Xu Deng","doi":"10.1055/a-2343-0881","DOIUrl":"https://doi.org/10.1055/a-2343-0881","url":null,"abstract":"Cage-like polycycles represent a class of structurally unique and biologically promising molecules. Whereas, efficient synthetic approaches are quite rare. This work disclosed the RhI-catalysed cycloisomerization reactions of 1,7-enynes containing a chelating group at the alkyne terminus, which afforded the unprecedented cage-like tricyclo[3.2.2.06,8]-nonenes via unprecedented 7-endo-dig cyclization. This work not only provides a straightforward approach to this novel cage-like tricycles, but also unveils the underexplored π-acidic reactivity of RhI catalyst with the assistance of secondary chelation.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141356494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stereoselective Synthesis of Azobenzene-Based Glycomacrocycles 偶氮苯基糖环的立体选择性合成
Synthesis Pub Date : 2024-06-11 DOI: 10.1055/s-0043-1774911
Jinbiao Jiao, Juan Xie
{"title":"Stereoselective Synthesis of Azobenzene-Based Glycomacrocycles","authors":"Jinbiao Jiao, Juan Xie","doi":"10.1055/s-0043-1774911","DOIUrl":"https://doi.org/10.1055/s-0043-1774911","url":null,"abstract":"<p>Carbohydrate-based macrocyclic compounds are of particular interest because of their multifunctionality, their unique structural and physicochemical properties as well as their potential applications in chemistry, biology, and drug discovery. Introducing a molecular photoswitch into the skeleton of glycomacrocycles makes possible the reversible control of properties of the resulting photoswitchable glycomacrocycles by light illumination. Therefore, development of stereoselective synthesis of this class of glycomacrocycles is of great interest. Two new azobenzene-based glycomacrocycles have been synthesized through an intramolecular glycosylation approach. Excellent 1,2-<i>cis</i> stereoselectivity has been achieved for the mannosylation.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528664","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 in Gold-Catalyzed Transformations of Vinyldiazo Reagents 金催化乙烯基二偶氮试剂转化的最新进展
Synthesis Pub Date : 2024-06-11 DOI: 10.1055/a-2343-1001
Olaya Bernardo, Patricia García-Martínez, Javier Santamaría, Luis A López
{"title":"Recent Advances in Gold-Catalyzed Transformations of Vinyldiazo Reagents","authors":"Olaya Bernardo, Patricia García-Martínez, Javier Santamaría, Luis A López","doi":"10.1055/a-2343-1001","DOIUrl":"https://doi.org/10.1055/a-2343-1001","url":null,"abstract":"Since the seminal report by Liu and coworkers in 2011, gold-catalyzed transformations of vinyldiazo compounds have become an important synthetic tool allowing the identification of new reaction patterns that have greatly expanded the versatility of these reagents. In this short review, we aim to showcase the most relevant advances in this exciting research topic.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141355576","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Rh(III)-Catalyzed Redox-neutral C-H Multifluoroalkenylation of Benzamides Rh(III)催化的苯甲酰胺氧化还原中性 C-H 多氟烯化反应
Synthesis Pub Date : 2024-06-11 DOI: 10.1055/a-2343-0676
Jia-Qiang Wu, Wei Lin, Yifei Qu, Mei Xie, Huixuan Zhu, Jinhui Hu, Zhuang Xiong, Jun Xu, Wenhua Chen
{"title":"Rh(III)-Catalyzed Redox-neutral C-H Multifluoroalkenylation of Benzamides","authors":"Jia-Qiang Wu, Wei Lin, Yifei Qu, Mei Xie, Huixuan Zhu, Jinhui Hu, Zhuang Xiong, Jun Xu, Wenhua Chen","doi":"10.1055/a-2343-0676","DOIUrl":"https://doi.org/10.1055/a-2343-0676","url":null,"abstract":"Fluorinated molecules are widely used in pharmaceutical and agrochemical industries. Multifluoroalkyl-containing compounds have attracted increasing attention for their unique ability to alter the activity of drugs and bioactive molecules. Herein, we report an efficient Rh(III)-catalyzed redox-neutral C-H multifluoroalkenylation of benzamides with multifluoroalkenes, which provides a versatile protocol for accessing a wide range of multifluoroalkenylated arenes.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141356833","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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