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Titanium Catalyzed the Cross-Coupling of Nitriles and Alkyl Halides for the Synthesis of Ketones 钛催化腈和烷基卤化物的交叉偶联以合成酮类化合物
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-10 DOI: 10.1002/adsc.202500222
Fanxiang Zeng, Biao Ma, Yiru Wang, Haocong Li, Minghui Zhang, Zhanyu Li
{"title":"Titanium Catalyzed the Cross-Coupling of Nitriles and Alkyl Halides for the Synthesis of Ketones","authors":"Fanxiang Zeng, Biao Ma, Yiru Wang, Haocong Li, Minghui Zhang, Zhanyu Li","doi":"10.1002/adsc.202500222","DOIUrl":"https://doi.org/10.1002/adsc.202500222","url":null,"abstract":"Here, a titanium-catalyzed cross-coupling of alkyl halides with nitriles under mild reaction conditions for the synthesis of ketones is reported. This reaction is applicable in benzyl halides, allyl halides, which are inactive substrates in the past reports, as well as non-activated alkyl halides. Mechanistic studies have suggested that titanium(III) acts both as a carbon radical initiator and a cyanoactivator. The gram-scale and derivatisation experiments also further demonstrate the potential application of the methodology.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813913","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
Development of Photo-Biocatalytic Redox System for Asymmetric Synthesis of Optically Active Amines Using Blue Light and Transaminases. A Case Study Toward Mavacamten 利用蓝光和转氨酶开发用于光学活性胺不对称合成的光生物催化氧化还原系统。针对马伐卡滕的案例研究
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-10 DOI: 10.1002/adsc.202500250
Natalia Antos, Aleksandra Rudzka, Anna Hoser, Tamara Reiter, Wolfgang Kroutil, Paweł Borowiecki
{"title":"Development of Photo-Biocatalytic Redox System for Asymmetric Synthesis of Optically Active Amines Using Blue Light and Transaminases. A Case Study Toward Mavacamten","authors":"Natalia Antos, Aleksandra Rudzka, Anna Hoser, Tamara Reiter, Wolfgang Kroutil, Paweł Borowiecki","doi":"10.1002/adsc.202500250","DOIUrl":"https://doi.org/10.1002/adsc.202500250","url":null,"abstract":"Abstract. α-Chiral amines are versatile building blocks for the asymmetric synthesis of optically pure high-added-value chemicals, including pharmaceuticals, agrochemicals, and natural products. Herein, we report a one-pot, two-step sequential deracemization of racemic sec-alcohols to optically enriched primary amines throught a photo-biocatalytic oxidation-reductive amination linear cascade. In the first step, near-to-quantitative oxidation of a set of racemic (hetero)benzylic alcohols into prochiral ketones was accomplished using visible light photoredox catalysis relying on 440 nm blue LEDs irradiation, 9-fluorenone as a transition-metal-free photocatalyst, and O2-saturated dimethyl sulfoxide (DMSO) as the reaction medium and a quencher of the in situ generated hydrogen peroxide (H2O2). The intermediary ketones were further converted into the corresponding non-racemic amines with up to >99% conversion, high-to-excellent optical purity (90−99.9% ee), and complementary absolute configuration via a stereoselective reductive amination catalyzed by lyophilized E. coli cells containing the respective (R)- or (S)- selective recombinant transaminases (E. coli/TAs) in an aqueous KPi buffer in the presence of pyridoxal-5'-phosphate (PLP) as cofactor and isopropylamine (iPrNH2) as an amino group donor. The developed photo-biocatalytic system was scaled up for racemic 1-phenylethanol (1.0 mmol), furnishing (S)-(−)-1-phenylethylamine with 91% conv., 82% isolated yield and 99% ee. An exemplary functionalization of the obtained (S)-α-methylbenzylamine with 6-chloro-3-isopropylpyrimidine-2,4(1H,3H)-dione led to afford an enantiomerically enriched newly launched cardiac-specific myosin inhibitor mavacamten in 76% yield and 99% ee. In addition, a single-crystal X-ray diffraction (XRD) analysis was performed, furnishing the first crystal structure for the titled API.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"59 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813980","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
Sustainable Synthesis of Quinazolinones through Boiler Flue Gas CO₂ Utilization via Pd@POP-1 Catalyst under Mild Conditions 温和条件下Pd@POP-1催化锅炉烟气CO 2可持续合成喹唑啉酮
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-10 DOI: 10.1002/adsc.202500238
Ying Liang, Kai-Zhi Xv, Pei-Bo Chen, Ping Fang, Jian Huang, Ying-ming Pan
{"title":"Sustainable Synthesis of Quinazolinones through Boiler Flue Gas CO₂ Utilization via Pd@POP-1 Catalyst under Mild Conditions","authors":"Ying Liang, Kai-Zhi Xv, Pei-Bo Chen, Ping Fang, Jian Huang, Ying-ming Pan","doi":"10.1002/adsc.202500238","DOIUrl":"https://doi.org/10.1002/adsc.202500238","url":null,"abstract":"A catalyst, Pd@POP-1, has been successfully synthesized by embedding palladium (Pd) nanoparticles into a nitrogen-rich porous organic polymer (POP) through the copolymerization of imidazole and triazine ionic salts with divinylbenzene. This catalyst features a unique imine (-C=N) structure within the triazine ring and multiple coupled imine groups, which significantly enhances CO2 adsorption efficiency and exhibits remarkable catalytic performance. At ambient pressure and mild temperatures, Pd@POP-1 effectively converts low-concentration CO2 (less than 15 vol.%) into quinazolinones, even in the presence of SO2 (up to 428 mg/m³) and NO2 (up to 221 mg/m³), achieving high yields. Remarkably, Pd@POP-1 also efficiently transforms CO2 from boiler flue gas, which contains 10 vol.% CO2, into quinazolinones with satisfactory yields. This approach not only provides an eco-friendly alternative for quinazolinone production by replacing phosgene with actual flue gas as a carbon source but also represents a promising strategy for the resource utilization of CO2 in flue gas.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"39 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143819959","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
Electrochemical Selective Benzylic C(sp3)–H Amination of Amino Group-Substituted Alkylarenes with Benzimidazoles 氨基取代烷基芳烃与苯并咪唑的电化学选择性C(sp3) -H胺化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-10 DOI: 10.1002/adsc.202500251
Yu-Wei Jiang, Peng-Zhan Zhang, Xiang Sun, Hui Gao, Pei-Long Wang
{"title":"Electrochemical Selective Benzylic C(sp3)–H Amination of Amino Group-Substituted Alkylarenes with Benzimidazoles","authors":"Yu-Wei Jiang, Peng-Zhan Zhang, Xiang Sun, Hui Gao, Pei-Long Wang","doi":"10.1002/adsc.202500251","DOIUrl":"https://doi.org/10.1002/adsc.202500251","url":null,"abstract":"An electrochemical benzylic C(sp3)–H amination reaction of amino group-substituted alkylarenes with benzimidazoles was developed. The reaction showed good selectivity, and C-H cleavage occurred selectively at the benzylic position other than the α-position of the amino group. Atom- and step-economic, catalyst-free, external oxidant-free, H2 as the only and clean byproduct are the additional characteristics of this electrochemical reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"39 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143814337","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 Radical Chemistry of Alkylboronic Acids and Derivatives 烷基硼酸及其衍生物自由基化学研究进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-09 DOI: 10.1002/adsc.202500191
Akash Bisoyi, Ananthakrishna Panuganti, Ramsiya Poolamanna, Alisha Rani Tripathy, V. Reddy Yatham
{"title":"Recent Advances in the Radical Chemistry of Alkylboronic Acids and Derivatives","authors":"Akash Bisoyi, Ananthakrishna Panuganti, Ramsiya Poolamanna, Alisha Rani Tripathy, V. Reddy Yatham","doi":"10.1002/adsc.202500191","DOIUrl":"https://doi.org/10.1002/adsc.202500191","url":null,"abstract":"Due to their versatility and stability, alkylboronic acids and their derivatives have emerged as valuable reagents in organic synthesis, particularly in radical chemistry for constructing diverse carbon-carbon and carbon-heteroatom bonds. Recent advancements have expanded their applications, enabling the generation of alkyl radicals under milder conditions, safely and cost-effectively. This mini-review focuses on recent advances in the methods by which radicals are generated from alkylboronic acids and derivatives, with a special focus on the reaction mechanism and applications of the methodology to different classes of reactions. We hope this review will enrich the knowledge and help further design and development in radical-based organic transformations using alkyl boronic acid and derivatives.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"172 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143814339","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
Tunable Preparation of β‐Substituted Alkenoate Esters via Radical Alkenylation of C(sp3)–H Bonds with Allenoates 丙烯酸盐与C(sp3) -H键自由基烯化制备β -取代烯酸酯的研究
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-08 DOI: 10.1002/adsc.202500012
Alexandra Jorea, Roberto Chessa, Davide Ravelli
{"title":"Tunable Preparation of β‐Substituted Alkenoate Esters via Radical Alkenylation of C(sp3)–H Bonds with Allenoates","authors":"Alexandra Jorea, Roberto Chessa, Davide Ravelli","doi":"10.1002/adsc.202500012","DOIUrl":"https://doi.org/10.1002/adsc.202500012","url":null,"abstract":"A photocatalytic strategy for the radical alkenylation of aliphatic C(<i>sp</i><sup>3</sup>)–H bonds with 2,3‐allenoate esters is described. The protocol takes place upon irradiation of the reaction mixture in the presence of the decatungstate anion, which triggers C–H cleavage in the chosen aliphatic substrates. The photogenerated C‐centered radicals add regioselectively to the central C(<i>sp</i>)‐atom of the cumulenic structure, delivering an allyl‐type radical adduct that finally leads to the β‐substituted alkenoate ester of interest. When an aliphatic allenoate is adopted, the protocol leads to the selective formation of a β,γ‐alkenoate, while the corresponding phenyl ester delivers a mixture of β,γ‐ and α,β‐alkenoates. Rationalization of the observed regioselectivity is supported by computational work, which highlights how the steric demand of the allenoate ester at the radical adduct level determines the reaction outcome. The versatility of the protocol, which can also take place under (telescoped) flow conditions, is further demonstrated by the possibility to divert the reaction outcome toward the selective formation of β,γ‐ or α,β‐alkenoate esters by performing the photocatalyzed process alone or in combination with a subsequent base‐promoted C=C double bond migration, respectively.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"74 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143805613","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 Assembly of Organoselenyl-Substituted (Thio)Chromones and 4-Quinolones 有机硒基取代（硫代）铬与4-喹诺酮类化合物的合成研究进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-08 DOI: 10.1002/adsc.202500210
Jinhui Cai, Zhouting Zeng, Qiaolin Wang, Weishuang Li
{"title":"Recent Advances in the Assembly of Organoselenyl-Substituted (Thio)Chromones and 4-Quinolones","authors":"Jinhui Cai, Zhouting Zeng, Qiaolin Wang, Weishuang Li","doi":"10.1002/adsc.202500210","DOIUrl":"https://doi.org/10.1002/adsc.202500210","url":null,"abstract":"Organoselenylated chromones, thiochromones, and 4-quinolones, as an important members of selenyl-bearing heterocycles, present significant biological activities. A variety of methods for the facile synthesis of selenyl-substituted chromones, thiochromones, and 4-quinolones, employ chromones, 2-hydroxyaryl enaminones, alknyl aryl ketones, and 4-quinolones as the starting material via transition-metal-catalyzed, oxidant-promoted, electrocatalytic, and photo-induced selenylation or selenocyanation, and cascade selenylation or selenocyanation/cyclization involving a radical pathway or cationic pathway, which are mainly summarized in this review. The detailed mechanism and the existed limitations of the reported strategies are also discussed here. Additionally, future prospects in the construction of organoselenyl-substituted chromones, thiochromones, and 4-quinolones, is showed to encourage chemists to push the development of heterocyclic chemistry and organoselenium chemistry.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"108 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143806378","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
Front Cover Picture: (Adv. Synth. Catal. 7/2025) 封面图片：（合成人广告）Catal。7/2025)
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-08 DOI: 10.1002/adsc.202580701
{"title":"Front Cover Picture: (Adv. Synth. Catal. 7/2025)","authors":"","doi":"10.1002/adsc.202580701","DOIUrl":"https://doi.org/10.1002/adsc.202580701","url":null,"abstract":"<p>As of 2025, Advanced Synthesis and Catalysis joins the Advanced Portfolio from Wiley. Led by the world-renowned journal Advanced Materials, the Advanced Portfolio is a family of globally respected, high-impact journals that disseminate the best science. With the inclusion of Advanced Synthesis and Catalysis, it is broadening its reach into the field of chemistry. Cover image provided courtesy of Liang Zhao and co-workers from Dalian University of Technology.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 7","pages":""},"PeriodicalIF":4.4,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202580701","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143793621","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Developments in Radical Mediated Synthesis of Organostannanes 有机硅烷自由基介导合成研究进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-08 DOI: 10.1002/adsc.202500243
Qianhang Ren, Adrian Luguera Ruiz, Maurizio Fagnoni, Stefano Protti, Di Qiu
{"title":"Recent Developments in Radical Mediated Synthesis of Organostannanes","authors":"Qianhang Ren, Adrian Luguera Ruiz, Maurizio Fagnoni, Stefano Protti, Di Qiu","doi":"10.1002/adsc.202500243","DOIUrl":"https://doi.org/10.1002/adsc.202500243","url":null,"abstract":"The present review aims to provide an overview of the recent developments in the preparation of aryl‐ or alkenyl stannanes via carbon‐ and tin‐centered radicals enabling chemists to synthesize organostannyl derivatives with high efficiency and under mild conditions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"17 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143805614","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
Intermolecular 1,4‐Difunctionalization of Conjugated Dienes Enabled by Palladium/Copper/Iodide Cooperation: Regioselective Construction of 3‐Pyrrolines 通过钯/铜/碘合作实现共轭二烯的分子间 1,4-二官能化：3-Pyrrolines 的区域选择性构建
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-08 DOI: 10.1002/adsc.202500125
Jingjie Meng, Junwei Wang, Jingang Zhang, Zhengxing Wu, Zehua Yang, Wanbin Zhang
{"title":"Intermolecular 1,4‐Difunctionalization of Conjugated Dienes Enabled by Palladium/Copper/Iodide Cooperation: Regioselective Construction of 3‐Pyrrolines","authors":"Jingjie Meng, Junwei Wang, Jingang Zhang, Zhengxing Wu, Zehua Yang, Wanbin Zhang","doi":"10.1002/adsc.202500125","DOIUrl":"https://doi.org/10.1002/adsc.202500125","url":null,"abstract":"3‐Pyrrolines are important nitrogen‐containing five‐membered heterocycles. In recent years, significant progress has been made in developing synthetic methods for 3‐pyrrolines, including direct and efficient strategy for the 1,4‐difunctionalization of conjugated dienes. However, most existing approaches typically require pre‐activated nitrogen sources (nitrene precursor or imine) or rely on intramolecular reactions to enhance reactivity, enabling the construction of 3‐pyrrolines. The synthesis of 3‐pyrrolines via intermolecular reactions without using pre‐activated nitrogen sources remains a challenging task. In this study, we present an intermolecular 1,4‐difunctionalization of conjugated dienes for the synthesis of 3,4‐disubstituted 3‐pyrrolines, using a tosylamide (NH&lt;sub&gt;2&lt;/sub&gt;Ts) as the nitrogen source. The reaction was facilitated through the cooperation of palladium(II), copper(I) and iodide. The resulting 3‐pyrrolines can be readily converted into various pyrroles and pyrrolidines through simple transformations.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"100 29-30 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143805615","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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