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Cobalt-Catalyzed Enantioselective Alkenylative Cyclization of 1,6-Allenynes 钴催化的 1,6-Allenynes 对映体选择性烯丙基环化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-17 DOI: 10.1002/adsc.202500022
Tao Wang, Ji-Xun Guan, Yun-Xuan Tan, Ping Tian
{"title":"Cobalt-Catalyzed Enantioselective Alkenylative Cyclization of 1,6-Allenynes","authors":"Tao Wang, Ji-Xun Guan, Yun-Xuan Tan, Ping Tian","doi":"10.1002/adsc.202500022","DOIUrl":"https://doi.org/10.1002/adsc.202500022","url":null,"abstract":"Transition metal-catalyzed cascade cyclization of allenynes is regarded as an efficient approach for the synthesis of versatile cyclic frameworks. However, catalytic asymmetric cascade cyclizations of allenynes are still uncommon. Herein, we present the first cobalt-catalyzed enantioselective alkenylative cyclization of 1,6-allenynes with readily available alkenylboronic acids, providing five-membered carbo- and heterocycles with high efficiency (up to 97% yield), broad substrate scope, and moderate to good enantioselectivities (up to 95:5 er).","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"38 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846453","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 Hydrofluoroolefin (HFO)-based direct O-fluoroalkenylation of phenols targeting tyrosine conjugation 以酪氨酸偶联为目标的基于氢氟烯烃（HFO）的酚类直接o -氟烯化反应的研究进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-17 DOI: 10.1002/adsc.202500282
Rihárd Sisa, Ferenc Béke, Zoltán Novák
{"title":"Development of Hydrofluoroolefin (HFO)-based direct O-fluoroalkenylation of phenols targeting tyrosine conjugation","authors":"Rihárd Sisa, Ferenc Béke, Zoltán Novák","doi":"10.1002/adsc.202500282","DOIUrl":"https://doi.org/10.1002/adsc.202500282","url":null,"abstract":"Methodology for direct fluoroalkenylation of phenolic OH function was developed using a fluorinated electrophilic reagent derived from HFO1234ze gas. Besides various functionalized phenols, tyrosine and tyrosine-based peptides were successfully conjugated under the optimized reaction conditions. Furthermore, the transformability of the fluoroalkenyl bromide motif was demonstrated to expand the space of bioconjugation via palladium catalyzed cross-coupling reactions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"27 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846544","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
Metal‐Free Divergent Photocatalytic Cascade [4+2] Addition‐Defluorinative Annulation of gem‐Difluoroalkenes with Terminal Alkynes 无金属发散光催化级联[4+2]宝石-二氟烯烃与末端炔的加成-去氟环化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-17 DOI: 10.1002/adsc.202500314
Dong-Sheng Li, Guang-Xu Zhang, Hao Qian, Fei Xue, Hong-Ping Deng
{"title":"Metal‐Free Divergent Photocatalytic Cascade [4+2] Addition‐Defluorinative Annulation of gem‐Difluoroalkenes with Terminal Alkynes","authors":"Dong-Sheng Li, Guang-Xu Zhang, Hao Qian, Fei Xue, Hong-Ping Deng","doi":"10.1002/adsc.202500314","DOIUrl":"https://doi.org/10.1002/adsc.202500314","url":null,"abstract":"A mild, metal‐free protocol for cascade [4+2] addition‐defluorinative annulation of gem‐difluoroalkenes with alkynes was realized via photoredox catalysis. This method was feasible for a wide range of terminal alkynes, affording the 1,3‐cyclohexadiene derivatives or fluoro‐substituted arenes in moderate to good yields, respectively. The merit of this strategy was demonstrated by the late‐stage functionalization of pharmaceuticals and the synthesis of high‐value‐added complex molecules.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"49 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842112","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 Annulation Reactions of α,β-Unsaturated Ketoximes for the Synthesis of Structurally Diversified Heterocycles α，β-不饱和酮肟合成结构多样化杂环的环化反应研究进展
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-17 DOI: 10.1002/adsc.202500259
Gaochen Xu, Yongfang Wang, Yan Meng, Zheng Fang, Duan Jindian, Kai Guo
{"title":"Recent Advances in Annulation Reactions of α,β-Unsaturated Ketoximes for the Synthesis of Structurally Diversified Heterocycles","authors":"Gaochen Xu, Yongfang Wang, Yan Meng, Zheng Fang, Duan Jindian, Kai Guo","doi":"10.1002/adsc.202500259","DOIUrl":"https://doi.org/10.1002/adsc.202500259","url":null,"abstract":"Transition metal-catalyzed or metal-free-mediated annulation of α,β-unsaturated ketoximes with unsaturated coupling partners has emerged as a powerful protocol for the assembly of diverse functionalized heterocycles, which is attributed to the ability of the oxime functionality to serve as a directing group for C−H activation, to undergo reductive N−O bond cleavage, and be activated by Lewis acids or reduced by iodide salts. In this review, we summarize the coupling reactions of three types of α,β-unsaturated ketoximes with various organic compounds containing unsaturated bonds such as alkenes, alkynes, carbonyls, nitriles and so on over the past decades. The reaction conditions, selected examples of the reaction scope, limitations, and reasonable mechanisms are critically described. Furthermore, the prospects for future challenges and opportunities are also explored.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"29 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842104","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
Chemoselective Synthesis of α‐Chloro and α,α ‐Dichloro acetamidines via the Carbenoids Addition to Inherently Low Electrophilic Carbodiimides 低亲电性碳二酰亚胺加羰基化合物化学选择性合成α -氯和α，α -二氯乙酰脒
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-17 DOI: 10.1002/adsc.202500320
Davide Castiglione, Margherita Miele, Alberto Nardi, Laura Castoldi, Vittorio Pace
{"title":"Chemoselective Synthesis of α‐Chloro and α,α ‐Dichloro acetamidines via the Carbenoids Addition to Inherently Low Electrophilic Carbodiimides","authors":"Davide Castiglione, Margherita Miele, Alberto Nardi, Laura Castoldi, Vittorio Pace","doi":"10.1002/adsc.202500320","DOIUrl":"https://doi.org/10.1002/adsc.202500320","url":null,"abstract":"The hitherto few explored α‐halomethyl amidine motif has been assembled through the addition of a lithiated (di)‐halomethane (i.e. carbenoid) to easily accessible N,N’‐diaryl substituted carbodiimides. Despite the inherent low electrophilicity of these heterocumulenes – as quantitatively determined in Mayr’s previous studies – their sp‐hybridized carbon atom acts as a competent site of attack for these tamed nucleophiles. The overall high‐yielding transformation featuring a genuine chemoselective profile – as documented by employing variously functionalized materials – is adaptable to the addition of dihalogenated carbenoids. Reaction products could be advantageously employed in nucleophilic substitution sequences, as well as, in further functionalization of the nitrogen atoms due to the constitutive heteroallyl‐type skeleton.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842125","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
Alkylation of Imines with Alkyl Halides under Electrochemical Conditions 电化学条件下亚胺与卤代烃的烷基化反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI: 10.1002/adsc.202401527
Tan Zhang , Mengyun Wu , Wenhui Wang , Yingsibing Fan , Ping Liu , Peipei Sun
{"title":"Alkylation of Imines with Alkyl Halides under Electrochemical Conditions","authors":"Tan Zhang ,&nbsp;Mengyun Wu ,&nbsp;Wenhui Wang ,&nbsp;Yingsibing Fan ,&nbsp;Ping Liu ,&nbsp;Peipei Sun","doi":"10.1002/adsc.202401527","DOIUrl":"10.1002/adsc.202401527","url":null,"abstract":"<div><div>An electrochemical protocol for the alkylation of imines was developed by using easily available alkyl halides as the alkyl sources, graphite felt (GF) as anode and zinc plate as cathode. Various substituted imines, alkyl bromides and alkyl iodides were suitable for this reaction and a series of α‐branched amines were obtained in moderate to good yields. This method provides a green way for the addition of imines to avoid the need for metal reagents, chemical oxidants and reductants, which makes it has a good application prospect in drug synthesis.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 8","pages":"Article e202401527"},"PeriodicalIF":4.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142992471","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
Palladium/Norbornene Cooperative Catalysis: A Modular In Situ Vicinal Functionalization Strategy for Recent Developments of Carbohydrate Chemistry 钯/降冰片烯协同催化：碳水化合物化学最新进展的模块化原位邻近功能化策略
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI: 10.1002/adsc.202401570
Himanshu Gangwar , Zanjila Azeem , Pintu Kumar Mandal
{"title":"Palladium/Norbornene Cooperative Catalysis: A Modular In Situ Vicinal Functionalization Strategy for Recent Developments of Carbohydrate Chemistry","authors":"Himanshu Gangwar ,&nbsp;Zanjila Azeem ,&nbsp;Pintu Kumar Mandal","doi":"10.1002/adsc.202401570","DOIUrl":"10.1002/adsc.202401570","url":null,"abstract":"<div><div>The palladium/norbornene (Pd/NBE) cooperative catalysis, first identified by Catellani in 1997, provides an efficient approach for synthesizing highly functionalized aromatic compounds that are challenging to obtain through conventional methods. The developed synthetic approach integrates selective C−H bond activation with sequential reactions, allowing for the targeted functionalization of both the <em>ortho</em> and <em>ipso</em> positions of aryl halides via aryl‐norbornadiene‐palladacycle (ANP), which in turn ensures high chemoselectivity and regioselectivity of the products. It is estimated that approximately 20% of all natural products are glycosylated, with the carbohydrates linked to these compounds frequently playing a critical role in their biological activity. Currently, research in carbohydrate chemistry predominantly concentrates on polysubstitutional derivatization or vicinal functionalization strategies. However, the limited availability of 1,2‐disubstituted compounds has been scarcely investigated, and previous studies often relied on directional group assistance to achieve disubstitution. Recently, significant advancements have been achieved with Pd/NBE cooperative catalysis, an area that has gained considerable importance in carbohydrate chemistry, presenting an opportunity to inspire further research interest in Catellani reactions. In this review, we provide a comprehensive analysis of the Pd/NBE strategy within the realm of sugar chemistry, encompass early research and advancement in catalytic reactions, outline synthetic potential, highlight the significant progress made, and emphasize the most recent developments and their applications in situ vicinal functionalization of carbohydrate derivatives.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 8","pages":"Article e202401570"},"PeriodicalIF":4.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435400","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
Synthesis of Chiral 2‐trifluoromethyl‐4‐(tetrahydroquinolinyl)‐4H‐chromenes via Pd‐Catalyzed Asymmetric Amination 通过钯催化不对称胺化合成手性 2-三氟甲基-4-(四氢喹啉基)-4H-苯并吡喃
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI: 10.1002/adsc.202401422
Bangzhong Wang , Luyang Sun , Pengyue Zhang , Shuaibo Zhang , Jinfeng Zhao , Jingping Qu , Yuhan Zhou
{"title":"Synthesis of Chiral 2‐trifluoromethyl‐4‐(tetrahydroquinolinyl)‐4H‐chromenes via Pd‐Catalyzed Asymmetric Amination","authors":"Bangzhong Wang ,&nbsp;Luyang Sun ,&nbsp;Pengyue Zhang ,&nbsp;Shuaibo Zhang ,&nbsp;Jinfeng Zhao ,&nbsp;Jingping Qu ,&nbsp;Yuhan Zhou","doi":"10.1002/adsc.202401422","DOIUrl":"10.1002/adsc.202401422","url":null,"abstract":"<div><div>A new strategy for the construction of chiral 4<em>H</em>‐chromene skeleton via Pd‐catalyzed asymmetric amination of <em>2H</em>‐chromene was reported. A series of chiral 2‐trifluoromethyl‐4<em>H</em>‐chromenes containing 1,2,3,4‐tetrahydroquinoline unit were synthesized in moderate to good yields with excellent enantioselectivity, the method serves as an effective supplement to the construction of chiral 4<em>H</em>‐chromene skeleton.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 8","pages":"Article e202401422"},"PeriodicalIF":4.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832627","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
Iron‐Catalyzed Decarboxylative and Deconstructive Cross‐Coupling of Acrylic Acids with Ketone‐Derived Dihydroquinazolinones 铁催化的丙烯酸与酮类二氢喹唑啉酮的脱羧和解构交叉偶联
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI: 10.1002/adsc.202401503
Xiao‐Yu Lu , Meng‐Xue Su , Hua‐Yi Huang , Yu‐Jun Qian , Hai‐Lun Sun , Xiang Li , Xin‐Ru Hu , Hao‐Yu Dong
{"title":"Iron‐Catalyzed Decarboxylative and Deconstructive Cross‐Coupling of Acrylic Acids with Ketone‐Derived Dihydroquinazolinones","authors":"Xiao‐Yu Lu ,&nbsp;Meng‐Xue Su ,&nbsp;Hua‐Yi Huang ,&nbsp;Yu‐Jun Qian ,&nbsp;Hai‐Lun Sun ,&nbsp;Xiang Li ,&nbsp;Xin‐Ru Hu ,&nbsp;Hao‐Yu Dong","doi":"10.1002/adsc.202401503","DOIUrl":"10.1002/adsc.202401503","url":null,"abstract":"<div><div>Herein, an iron‐catalyzed protocol for the aromatization‐driven deconstruction and decarboxylation of ketone‐derived dihydroquinazolinones in reaction with unsaturated carboxylic acids is reported. A diverse range of fluoroacrylic acids and cinnamic acids reacted effectively with dihydroquinazolinones, yielding essential monofluoroalkenes and alkenes with excellent stereoselectivity. Additionally, spiro‐dihydroquinazolinones served as suitable substrates, facilitating the synthesis of valuable quinazolin‐4(3H)‐ones featuring alkene motifs. This protocol is notable for its operational simplicity and versatility, enabling the chemical diversification of active molecules.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 8","pages":"Article e202401503"},"PeriodicalIF":4.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142981646","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
Preparation of Mesoporous Cu2O Nanospheres for Green Synthesis in the Enantioselective Boron Conjugate Addition of α,β‐Unsaturated Chiral Compounds in Aqueous Phase 介孔Cu₂O纳米球的制备及其在水相中对映选择性硼共轭加成α，β‐不饱和手性化合物的绿色合成
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI: 10.1002/adsc.202401501
Xuhong Zhao , Lian Ma , Meng Wang , Weishuang Li , Yaoyao Zhang , Bojie Li , Zhongpu Fang , Bo Xiong , Lei Zhu
{"title":"Preparation of Mesoporous Cu2O Nanospheres for Green Synthesis in the Enantioselective Boron Conjugate Addition of α,β‐Unsaturated Chiral Compounds in Aqueous Phase","authors":"Xuhong Zhao ,&nbsp;Lian Ma ,&nbsp;Meng Wang ,&nbsp;Weishuang Li ,&nbsp;Yaoyao Zhang ,&nbsp;Bojie Li ,&nbsp;Zhongpu Fang ,&nbsp;Bo Xiong ,&nbsp;Lei Zhu","doi":"10.1002/adsc.202401501","DOIUrl":"10.1002/adsc.202401501","url":null,"abstract":"<div><div>Chiral organoboron compounds are essential intermediates in various significant reactions. However, there are still few efficient catalysts for their synthesis. This paper reports a novel catalytic material for chiral asymmetric boron conjugate addition reactions: mesoporous Cu<sub>2</sub>O nanospheres (M−Cu<sub>2</sub>O). M−Cu<sub>2</sub>O is approximately 0.55 μm, exhibiting dense and uniformly distributed worm‐like pores. It features a specific surface area of 15.7 m<sup>2</sup>/g and an average pore size of 14.3 nm. Under the conditions of Toluene:H<sub>2</sub>O=9:1, with a chiral ligand amount of 3.6 mol% and no additional base, it achieves a high yield (98% yield) and impressive enantioselectivity (99% ee) for the template substrate chalcone using only 3.0 mol% of the catalyst. Notably, the catalyst can be easily recovered and maintains robust catalytic performance after seven cycles, yielding 92% and an ee value of 90%. This work presents a mild and effective method for synthesizing chiral boron compounds in an aqueous phase, significantly enhancing the application potential of mesoporous copper oxide nanospheres.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 8","pages":"Article e202401501"},"PeriodicalIF":4.4,"publicationDate":"2025-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142937431","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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