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Silver and Copper‐Catalyzed Cycloaddition Reactions of Isocyanide Esters 银和铜催化的异氰酸酯环加成反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-12 DOI: 10.1002/adsc.202400994
fatemeh doraghi, Parsa Baghershahi, Farzad Gilaninezhad, Negar Mehdi zadeh Darban, Navid Dastyafteh, Milad Noori, Mohammad Mahdavi
{"title":"Silver and Copper‐Catalyzed Cycloaddition Reactions of Isocyanide Esters","authors":"fatemeh doraghi, Parsa Baghershahi, Farzad Gilaninezhad, Negar Mehdi zadeh Darban, Navid Dastyafteh, Milad Noori, Mohammad Mahdavi","doi":"10.1002/adsc.202400994","DOIUrl":"https://doi.org/10.1002/adsc.202400994","url":null,"abstract":"Owing to multiple reactive sites, such as an acidic α‐carbon and an isocyano group, isocyanide esters can successfully participate in the synthesis of various five‐ and six‐membered N‐heterocycles through the cycloaddition reactions under metal‐catalyzed systems. Considering the unique and versatile functionality of this synthon, in this review, we have highlighted silver and copper‐catalyzed cycloadditions of isocyanide esters over the last decade.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"16 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142415740","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}
引用次数: 0
Methodology to Control the Regioselective Installation of a Carboxylic Acid for the Synthesis of 2,3-Diarylpropionic Acids 控制羧酸区域选择性安装以合成 2,3-二芳基丙酸的方法学
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-10 DOI: 10.1002/adsc.202400952
Mason Hamilton, Trina M. Perrone, Brian Popp
{"title":"Methodology to Control the Regioselective Installation of a Carboxylic Acid for the Synthesis of 2,3-Diarylpropionic Acids","authors":"Mason Hamilton, Trina M. Perrone, Brian Popp","doi":"10.1002/adsc.202400952","DOIUrl":"https://doi.org/10.1002/adsc.202400952","url":null,"abstract":"A stepwise copper-catalyzed boracarboxylation then palladium-catalyzed Suzuki-Miyaura cross-coupling methodology was developed to access 2,3-diarylpropionic acid derivatives regioselectively by pre-setting the position of the carboxylic acid in the boracarboxylation reaction. This method provides access to a wide range of aryl and heteroaryl products in up to 80% isolated yield. Pharmaceutical potential was demonstrated by synthesizing a glucagon receptor antagonist drug in 3-steps (31% overall yield) from commercially available 4-tert-butylstyrene.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"108 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398613","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}
引用次数: 0
Recent Advances in the Cascade Cyclization of Alkyne Units for the Construction of Benzofluorenes 用于制造苯并芴的炔烃单元级联环化的最新进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-10 DOI: 10.1002/adsc.202401047
Shimin Jiang, Ruchun Yang, Xian-Rong Song, qiang xiao
{"title":"Recent Advances in the Cascade Cyclization of Alkyne Units for the Construction of Benzofluorenes","authors":"Shimin Jiang, Ruchun Yang, Xian-Rong Song, qiang xiao","doi":"10.1002/adsc.202401047","DOIUrl":"https://doi.org/10.1002/adsc.202401047","url":null,"abstract":"Benzofluorenes are an important class of polycyclic aromatic hydrocarbons (PAHs), which are widely used in materials science for light-sensitive electronic components. In addition, the benzofluorene skeleton also serves as a key structural unit in various natural products. Therefore, the development of synthetic strategies for the construction of benzofluorenes has been a prominent research topic in synthetic chemistry. Over the past few decades, numerous efforts have been made for the construction of benzofluorenes via cascade cyclization of alkyne units. This review aims to summarize recent advances in the cascade cyclization of alkyne units for the construction of Based on the different reaction mechanisms underlying these transformations, this review can be divided into four categories: (1) thermal-induced cascade cyclization of alkyne units for the construction of benzofluorenes, (2) metal-catalyzed cascade cyclization of alkyne units for the construction of benzofluorenes, (3) acid-promoted/catalyzed cyclization of alkyne units for the construction of benzofluorenes, and (4) base-promoted cascade cyclization of alkyne units for the construction of benzofluorenes.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398607","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}
引用次数: 0
Fe(III)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes Improved by Using Triphenylphosphate as an Additive 使用三苯基膦作为添加剂改进铁（III）催化的 1,3-二烯分子内氢化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-10 DOI: 10.1002/adsc.202401180
Ye Jin Kim, Dong Bin Kim, So Won Youn
{"title":"Fe(III)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes Improved by Using Triphenylphosphate as an Additive","authors":"Ye Jin Kim, Dong Bin Kim, So Won Youn","doi":"10.1002/adsc.202401180","DOIUrl":"https://doi.org/10.1002/adsc.202401180","url":null,"abstract":"We herein report that the combination of Fe(OTf)3 and triphenylphosphate (TPP, (PhO)3PO) has proven to be an effective catalyst for the intramolecular hydroamination of amino-1,3-dienes with an efficiency and scope superior to previously reported methods. This catalytic system demonstrated consistent performance with diverse aminodienes as well as aminoolefins, providing five- to seven-membered N-heterocycles. We propose a Lewis/Brønsted acid cocatalysis mechanism involving proton transfer through hydrogen bonding with TPP. Catalyst system consisting of inexpensive and nontoxic iron salt and phosphate additive, relatively low loading and recyclability of catalyst, and rapid and high-yielding reaction are the advantages of this protocol.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"26 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398610","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}
引用次数: 0
Ni-Catalyzed [2+2+2] Cycloaddition of Alkynes to Form Arenes and Pyridines at Low Catalyst Loadings 镍催化炔烃的[2+2+2]环加成反应，在低催化剂添加量下生成烯和吡啶
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-09 DOI: 10.1002/adsc.202400765
María Trinidad Martín, Celia Maya, Agustin Galindo, M Carmen Nicasio
{"title":"Ni-Catalyzed [2+2+2] Cycloaddition of Alkynes to Form Arenes and Pyridines at Low Catalyst Loadings","authors":"María Trinidad Martín, Celia Maya, Agustin Galindo, M Carmen Nicasio","doi":"10.1002/adsc.202400765","DOIUrl":"https://doi.org/10.1002/adsc.202400765","url":null,"abstract":"We report the Ni-catalyzed cyclotrimerization of terminal alkynes at very low loadings of catalysts (0.05 mol% for all substrates). The nickel catalyst containing a terphenyl phosphine ligand allows carrying out the reactions at room temperature in only 30 min, providing the arene products as a single regioisomer in most cases The Ni complex is also competent for the synthesis of polysubstituted pyridines through the cycloadditions of diynes and nitriles at mild temperatures (25 º or 50 ºC) and low Ni loadings (1 mol%). Experimental data and computational studies support the involvement of monoligated PNi species in all fundamental steps of the catalytic cycle.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"43 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398093","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}
引用次数: 0
Gold-catalyzed Annulation between 1-[2-(Dimethoxymethyl)phenyl]prop-2-yn-1-yl Acetates and α-Diazoesters or Anilines to Form Substituted Naphthoates and Indeno[1,2-b]quinoline, Respectively. 金催化 1-[2-(二甲氧基甲基)苯基]丙-2-炔-1-基乙酸酯与 α-重氮酯或苯胺之间的环化反应，分别生成取代的萘酸盐和茚并[1,2-b]喹啉。
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-09 DOI: 10.1002/adsc.202400968
Rai-Shung Liu, Akshay Suresh Kshirsagar
{"title":"Gold-catalyzed Annulation between 1-[2-(Dimethoxymethyl)phenyl]prop-2-yn-1-yl Acetates and α-Diazoesters or Anilines to Form Substituted Naphthoates and Indeno[1,2-b]quinoline, Respectively.","authors":"Rai-Shung Liu, Akshay Suresh Kshirsagar","doi":"10.1002/adsc.202400968","DOIUrl":"https://doi.org/10.1002/adsc.202400968","url":null,"abstract":"This work describes gold-catalyzed annulations of 1-(2-(dimethoxymethyl)phenyl)-1-prop-2-yn-1-yl acetate substrates with α-diazo esters and anilines, respectively yielding substituted naphthoates and indeno[1,2-b]quinoline derivatives. Our mechanistic analysis indicates 1-methoxy-2-carbonyl-1H-indenes as their common intermediates. In the formation of naphthoates, α-diazo ester attacks at gold-bound intermediate via a SN2 pathway to enable a allylic methoxy substitution. For indeno[1,2-b]quinoline derivatives, there are two main reactions, including (i) a reversible formation between intermediate and a double amine addition product and (ii) an arylation reaction of intermediate. Species N-(phenyl((2E)-1-(phenylimino)-1,3-dihydro-2H-inden-2-ylidene)methyl)aniline was converted to indeno[1,2-b]quinoline in the presence of gold catalyst.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398551","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}
引用次数: 0
Copper Powder-Mediated Tandem Hydroamination Cyclization-Hydrocyanation of Alkyne-Tethered Ketoximes toward Cyano-Featured Cyclic Nitrones 铜粉介导的炔烃系酮肟的串联氢化环化-氢化氰化反应，生成具有氰基特征的环状硝基化合物
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-09 DOI: 10.1002/adsc.202401049
Wen-Jun Han, Fang-Long Yang, Zhiyuan Hu, Wenxia Chen, Shun Liu, Ke Guo, Xin-Yuan Yang, Bin Cheng
{"title":"Copper Powder-Mediated Tandem Hydroamination Cyclization-Hydrocyanation of Alkyne-Tethered Ketoximes toward Cyano-Featured Cyclic Nitrones","authors":"Wen-Jun Han, Fang-Long Yang, Zhiyuan Hu, Wenxia Chen, Shun Liu, Ke Guo, Xin-Yuan Yang, Bin Cheng","doi":"10.1002/adsc.202401049","DOIUrl":"https://doi.org/10.1002/adsc.202401049","url":null,"abstract":"The copper powder-mediated tandem hydroamination cyclization-hydrocyanation of alkyne-tethered ketoximes is described by using TMSCN as the commercially available cyanating reagent. This methodology provides an alternative strategy for the synthesis of a series of structurally important cyano-substituted cyclic nitrones. The hydrocyanation process exhibits distinct regioselectivity depending on the substituent pattern of the alkyne moiety. Moreover, the synthesized products were shown to be capable of undergoing various derivatization reactions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"32 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398094","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}
引用次数: 0
Diaryliodonium Salt-Mediated Radical Transformation of Indoles with Alcohols for the Synthesis of Unsymmetrical Bis(indolyl)methanes 二迭碘鎓盐介导的吲哚与醇的自由基转化，用于合成不对称的双（吲哚基）甲烷
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-09 DOI: 10.1002/adsc.202400827
Hongzhen Wang, Haohao Jiang, Shuizhen Lin, Shuoshuo Zhang, Xiaolei Huang
{"title":"Diaryliodonium Salt-Mediated Radical Transformation of Indoles with Alcohols for the Synthesis of Unsymmetrical Bis(indolyl)methanes","authors":"Hongzhen Wang, Haohao Jiang, Shuizhen Lin, Shuoshuo Zhang, Xiaolei Huang","doi":"10.1002/adsc.202400827","DOIUrl":"https://doi.org/10.1002/adsc.202400827","url":null,"abstract":"A method for the synthesis of unsymmetrical bis(indolyl)methanes (BIMs) using simple indoles and readily available alcohols as the coupling partners under both heat and 390–400 nm light conditions was developed. Detailed research of the mechanism demonstrated that the diaryliodonium salt-mediated transformation undergoes a nucleophilic hydroxymethyl radical formation process. Moreover, the diaryliodonium salt-mediated method is also applicable for synthesizing symmetrical BIMs.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"210 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142398095","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}
引用次数: 0
DMSO/SOCl2‐Mediated Synthesis of Thiomethylnaphthalenes from Propargyl Alcohols DMSO/SOCl2 介导的原炔醇硫代甲基萘合成反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-09 DOI: 10.1002/adsc.202401025
Zhihua Wang, Wang-Fu Liang, Xinglei He, Jingheng Li, Keyin Ye
{"title":"DMSO/SOCl2‐Mediated Synthesis of Thiomethylnaphthalenes from Propargyl Alcohols","authors":"Zhihua Wang, Wang-Fu Liang, Xinglei He, Jingheng Li, Keyin Ye","doi":"10.1002/adsc.202401025","DOIUrl":"https://doi.org/10.1002/adsc.202401025","url":null,"abstract":"Herein, we reported the straightforward synthesis of thiomethylnaphthalenes via the reaction of propargyl alcohols with DMSO/SOCl2, which also provided easy access to deuterated thiomethyl and other thioalkyl scaffolds when deuterated dimethyl sulfoxide and dialkyl sulfoxides were used, respectively. In addition, the thiomethyl group can be readily derivatized to the corresponding sulfoxide, sulfone, and sulfoximine of interesting photophysical properties.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385450","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}
引用次数: 0
Tropone hydrazides in [10+2]-hetero-higher-order cycloaddition for the synthesis of tetrahydropyridazine derivatives 用于合成四氢哒嗪衍生物的 [10+2]-hetero-higher-order cycloaddition 中的托品酰肼
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-10-08 DOI: 10.1002/adsc.202401033
Adam Cieśliński, Artur Przydacz, Lesław Sieroń, Anna Skrzyńska, Łukasz Albrecht
{"title":"Tropone hydrazides in [10+2]-hetero-higher-order cycloaddition for the synthesis of tetrahydropyridazine derivatives","authors":"Adam Cieśliński, Artur Przydacz, Lesław Sieroń, Anna Skrzyńska, Łukasz Albrecht","doi":"10.1002/adsc.202401033","DOIUrl":"https://doi.org/10.1002/adsc.202401033","url":null,"abstract":"[10+2]-Hetero-higher-order cycloaddition between tropone hydrazides (acting as 10π-components) and 3-alkylidene oxindoles (acting as 2π-components) has been established. Under Brønsted base catalysis the reaction proceeded in a fully peri- and diastereoselective manner with the stereochemical outcome governed mainly by electronic interactions. Following such a strategy, a series of structurally diverse tetrahydropyridazines were prepared in 30-70% yields. Furthermore, the potential of the obtained cycloadducts has been confirmed in selected chemoselective transformations.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"30 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385066","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}
引用次数: 0
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