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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
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
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
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
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
Homogeneous Copper-Catalyzed Cycloisomerization Reaction of Allenynes: Rapid Access to Functionalized Pyrroles 铜催化的均相烯炔环异构化反应：快速获得功能化吡咯
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500303
Kua-Fei Wei, Xiu-Hong Zhu, Guang-Xin Ru, Wen-Bo Shen
{"title":"Homogeneous Copper-Catalyzed Cycloisomerization Reaction of Allenynes: Rapid Access to Functionalized Pyrroles","authors":"Kua-Fei Wei, Xiu-Hong Zhu, Guang-Xin Ru, Wen-Bo Shen","doi":"10.1002/adsc.202500303","DOIUrl":"https://doi.org/10.1002/adsc.202500303","url":null,"abstract":"Homogeneous transition-metal-catalyzed alkyne cascade cyclization reaction has attracted much attentions over the past decades. However, the relevant homogeneous transition-metal-catalyzed cyclization of allenynes has seldom been explored probably due to noticeable chemo-, regio-, and stereoselectivity. Described herein is an efficient homogeneous copper-catalyzed cycloisomerization reaction of allenynes, thus leading to a practical and atom-economic access to an array of valuable functionalized pyrroles by formal [3 + 2] cycloaddition via Cu-containing all-carbon 1,4-dipoles.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"7 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832189","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
Illuminating the Path of Rearrangement: Visible Light-Driven Pd-Catalyzed Substituted Olefins Synthesis
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500161
jenifer Sharshonov, Valentin Duchemann, Yuqian Sun, Christine Tran, Philippe Belmont, Abdallah HAMZE, Diana Lamaa, Etienne BRACHET
{"title":"Illuminating the Path of Rearrangement: Visible Light-Driven Pd-Catalyzed Substituted Olefins Synthesis","authors":"jenifer Sharshonov, Valentin Duchemann, Yuqian Sun, Christine Tran, Philippe Belmont, Abdallah HAMZE, Diana Lamaa, Etienne BRACHET","doi":"10.1002/adsc.202500161","DOIUrl":"https://doi.org/10.1002/adsc.202500161","url":null,"abstract":"Pd-catalyzed reactions are among the most straightforward and efficient methods to proficiently build Csp2-Csp2 bonds. Nevertheless, thermal activation remains mandatory in most cases, which may decrease the compatibility with sensitive functional groups. In this context, improvements of conventional strategies must be an important source of research in order to enhance the applicability of such methods for building complex scaffolds. In this work, we contribute to this aim by implying visible-light as the sole energy source in a Pd-catalyzed rearrangement reaction involving N-tosylhydrazones and aryl halides. These mild reaction conditions efficiently allow oxidative addition, aryl migration and β-hydride elimination at room temperature, allowing the construction of various 1,1’ disubstituted olefins.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"23 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832190","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
Pot-Economical Synthesis of Fluorinated Pyrrolizinone Derivatives 氟化吡咯烷酮衍生物的锅内经济合成
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500209
Lidia Prieto, Marcos Escolano, Daniel Gaviña, Luis Paredes-Soler, Santiago Díaz Oltra, Maria Sanchez-Rosello, Carlos del Pozo
{"title":"Pot-Economical Synthesis of Fluorinated Pyrrolizinone Derivatives","authors":"Lidia Prieto, Marcos Escolano, Daniel Gaviña, Luis Paredes-Soler, Santiago Díaz Oltra, Maria Sanchez-Rosello, Carlos del Pozo","doi":"10.1002/adsc.202500209","DOIUrl":"https://doi.org/10.1002/adsc.202500209","url":null,"abstract":"A new family of fluorinated dihydropyrrolizinones has been synthesized starting from fluorinated enamino amides and aliphatic conjugated ketones. The reaction comprises a cross metathesis reaction followed by a tandem cycloaromatization/ enamine hydrolysis/ intramolecular Friedel-Crafts alkylation sequence. This pot-economical process takes place in good yields (35-67%), taking into account that it consists of four consecutive reactions. Aromatic enones are also good partners for this protocol although, in this case, the cross metathesis reaction has to be performed in a separated step.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"76 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832188","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 Polysubstitued Naphthalenes via Metal-free Borylative Cyclization of o-Alkynylstyrenes
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-14 DOI: 10.1002/adsc.202500244
Marcos Humanes, Manuel Ángel Fernández-Rodríguez, Patricia García-García
{"title":"Synthesis of Polysubstitued Naphthalenes via Metal-free Borylative Cyclization of o-Alkynylstyrenes","authors":"Marcos Humanes, Manuel Ángel Fernández-Rodríguez, Patricia García-García","doi":"10.1002/adsc.202500244","DOIUrl":"https://doi.org/10.1002/adsc.202500244","url":null,"abstract":"A selective, metal-free method for the synthesis of boron-functionalized polysubstituted naphthalenes via BCl₃-mediated cyclization of α-substituted o-alkynylstyrenes is described. The reaction exhibits broad substrate scope, tolerating various groups such as ethers, sulfides and halogens, and delivers high yields under mild conditions, even at gram scale. The resulting Bpin-functionalized naphthalenes serve as versatile building blocks, facilitating further transformations of the C–B bond into C–H, C–C, C–I, C–O, and C–N bonds, thereby increasing molecular complexity and enabling the design of more functionalized products.\u0000Notably, this sustainable and straightforward protocol selectively introduces the Bpin group at the sterically hindered α-carbon of the naphthalene framework, complementing C–H borylations of the naphthalene core, that preferentially occur at the β-position. As a result, the developed approach significantly broadens the accessibility of B-functionalized naphthalene derivatives for synthetic and application-oriented purposes.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143832187","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
Harnessing Nitroarenes in Streamlined Synthesis of 4‐Quinolones via Reductive C−N Coupling
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-04-11 DOI: 10.1002/adsc.202500393
Ni Dong, Xiao-Tian Zhang, Qin Tang, Jia-Xin Qian, Qi-Qi Luo, Long Cheng, Tian Cao, Xiang-Wei Liu
{"title":"Harnessing Nitroarenes in Streamlined Synthesis of 4‐Quinolones via Reductive C−N Coupling","authors":"Ni Dong, Xiao-Tian Zhang, Qin Tang, Jia-Xin Qian, Qi-Qi Luo, Long Cheng, Tian Cao, Xiang-Wei Liu","doi":"10.1002/adsc.202500393","DOIUrl":"https://doi.org/10.1002/adsc.202500393","url":null,"abstract":"The synthesis of quinolones is a key technology for the preparation of active pharmaceutical ingredients. Herein we present a step‐economical methodology for streamlined synthesis of 4‐quinolones from a tandem process involving a reduction of nitroarenes, an aza‐Michael addition and an intramolecular Buchwald‐Hartwig amination. This strategy uses synthetically upstream nitroarenes as viable aniline surrogates and B2pin2 as an enabling organic reductant, producing a wide range of 4‐quinolones bearing different functional groups in a step‐economical fashion. The potential value of this protocol is highlighted by late‐stage installation of 4‐quinolone moiety onto bioactive compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"60 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143818943","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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