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The Catalytic Synthesis of α-Bromo Aryl Acetic Acids by Late-Stage Bromination 通过后期溴化催化合成α-溴芳基乙酸
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-11-01 DOI: 10.1002/ejoc.202400962
Junyu Wang, Xin Wu, Beining Wang, Xiangyang Yuan, Shengnan Yang, Haipeng Hu
{"title":"The Catalytic Synthesis of α-Bromo Aryl Acetic Acids by Late-Stage Bromination","authors":"Junyu Wang, Xin Wu, Beining Wang, Xiangyang Yuan, Shengnan Yang, Haipeng Hu","doi":"10.1002/ejoc.202400962","DOIUrl":"https://doi.org/10.1002/ejoc.202400962","url":null,"abstract":"We report a catalytic late-stage bromination strategy for the α-C-H functionalization of aryl acetic acid. The aryl acetic acid was transformed into enediolate in the presence of an (AcO)4B2O with the combination of DBU, and consequently underwent an electrophilic bromination reaction with pyridinium tribromide. A wide range of α-bromo aryl acetic acids were isolated in yields of 19-65%. In addition, the reaction could be performed on a gram scale, and several transformations of the products were carried out.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"67 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142562175","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Silyl Radical-Participated Silylfunctionalization of Alkenes and Alkynes 硅烷自由基参与的烯烃和炔烃硅烷官能化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-31 DOI: 10.1002/ejoc.202401018
Yang Zheng, Yi-Jie Zhu, Yi-Nan Zhang, Fei Chen
{"title":"Silyl Radical-Participated Silylfunctionalization of Alkenes and Alkynes","authors":"Yang Zheng, Yi-Jie Zhu, Yi-Nan Zhang, Fei Chen","doi":"10.1002/ejoc.202401018","DOIUrl":"https://doi.org/10.1002/ejoc.202401018","url":null,"abstract":"Alkenes and alkynes are inexpensive and readily available basic chemicals. Silyl radical-participated silylation of alkenes and alkynes provides a powerful tool for the direct construction of organosilicon compounds. Compared to hydrosilylation reactions, silylfunctionalization reactions are more attractive and advantageous in building diverse organosilicon compounds, which has led to their becoming a research focus in organic synthesis. Herein, we provide a comprehensive overview of recent advances in silyl radical-participated silylfunctionalization of alkenes and alkynes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"319 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142562134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Organocatalytic Atroposelective C‐H Amination of Arenes with Indolines 烯与吲哚啉的有机催化无反选择性 C-H 氨基化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-31 DOI: 10.1002/ejoc.202401070
Jiangtao Sun, Tiantian Wang, Shaoran An
{"title":"Organocatalytic Atroposelective C‐H Amination of Arenes with Indolines","authors":"Jiangtao Sun, Tiantian Wang, Shaoran An","doi":"10.1002/ejoc.202401070","DOIUrl":"https://doi.org/10.1002/ejoc.202401070","url":null,"abstract":"An atroposelective synthesis of axially chiral N‐arylindolines has been established by organocatalytic nucleophilic amination of arenes with 7‐substituted indolines, providing a straightforward way to achieve the expected C‐N atropisomers in good yields (up to 95%) with good to excellent enantioselectivities (up to 97% ee) from readily available starting materials. Furthermore, axially chiral N‐arylindole derivatives could be prepared upon oxidative aromatization of the corresponding N‐arylindolines.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"116 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142561909","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 and selective transformation of aromatic thioether enabled by regulating active species under visible light irradiation 在可见光照射下通过调节活性物种实现芳香族硫醚的可调谐和选择性转化
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-30 DOI: 10.1002/ejoc.202401092
Meng-Ze Jia, Bin Tan, Yun-Rui Chen, Jia-Qi Pan, Shi-Kai Yu, Ling Xin, Jie Zhang
{"title":"Tunable and selective transformation of aromatic thioether enabled by regulating active species under visible light irradiation","authors":"Meng-Ze Jia, Bin Tan, Yun-Rui Chen, Jia-Qi Pan, Shi-Kai Yu, Ling Xin, Jie Zhang","doi":"10.1002/ejoc.202401092","DOIUrl":"https://doi.org/10.1002/ejoc.202401092","url":null,"abstract":"Through effective regulation of active species in photocatalytic process, the oxidation or C(sp3)-S bond cleavage upgrading of widespread aryl alkyl sulfides under mild conditions was successfully achieved by using a pyridinium photocatalyst. Benefiting from the excellent redox ability of the photocatalyst, the electron transfer between the pyridinium molecule and the substrate, molecular oxygen, or counter-anion effectively promotes the conversion and upgrading of the substrate thioether. Among them, the efficient generation of reactive oxygen species (ROS) enables the highly selective oxidation of sulfides to sulfoxides under visible light and air atmosphere. More importantly, the chlorine radical (Cl•) generated by electron transfer, reported for the first time, contributes to the cleavage of C(sp3)-S bonds, achieving the transformation of aryl alkyl sulfides to disulfides. By harnessing the superior photocatalytic ability of pyridinium molecules, this work not only achieves the highly selective conversion of thioether by taming the active species in the photocatalytic process, but also sheds light on the untapped potential of chlorine radicals in the field of C(sp3)-S bond activation and cleavage.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541981","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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-Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me4N][SeCF3] 铜介导的炔基羧酸与[Me4N][SeCF3]的三氟甲基硒化脱羧反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-30 DOI: 10.1002/ejoc.202400851
Xue Ding, Yu-Fei Yao, Jiang-Yu Li, Cheng-Pan Zhang
{"title":"Copper-Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me4N][SeCF3]","authors":"Xue Ding, Yu-Fei Yao, Jiang-Yu Li, Cheng-Pan Zhang","doi":"10.1002/ejoc.202400851","DOIUrl":"https://doi.org/10.1002/ejoc.202400851","url":null,"abstract":"The first decarboxylative trifluoromethylselenolation of alkynyl carboxylic acids with the nucleophilic [Me<sub>4</sub>N][SeCF<sub>3</sub>] salt was successfully accomplished by copper catalysis using air as an oxidant, furnishing the corresponding alkynyl trifluoromethyl selenoethers in good yields. Mechanistic studies revealed that the copper catalyst plays a key role in the oxidation of [Me<sub>4</sub>N][SeCF<sub>3</sub>] and the decarboxylation of alkynyl carboxylic acid for the subsequent trifluoromethylselenolation.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542057","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Diazo-Based Construction of Heterocyclic Systems Via a X−H Insertion/Cyclization Cascade 通过 X-H 插入/环化级联构建基于重氮的杂环系统
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-30 DOI: 10.1002/ejoc.202400909
Ksenia Malkova, Dmitry Dar'in
{"title":"Diazo-Based Construction of Heterocyclic Systems Via a X−H Insertion/Cyclization Cascade","authors":"Ksenia Malkova, Dmitry Dar'in","doi":"10.1002/ejoc.202400909","DOIUrl":"https://doi.org/10.1002/ejoc.202400909","url":null,"abstract":"This Concept outlines an X−H insertion/cyclization cascade (X=heteroatom), a prominent strategy for the assembly of N,O,S-heterocycles from diazo compounds and X−H-tethered precursors. While focusing on the cyclization via an addition to multiple bonds, we have highlighted Michael-type and Conia-ene reactions, aldol condensation, and Mannich reaction as prevalent ring-closing modes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541979","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Construction of Spiro Systems from Tetrathiafulvalene Derivatives by a Pinacol-like Rearrangement 通过类频哪醇重排从四噻吩甲醛衍生物构建螺系统
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-30 DOI: 10.1002/ejoc.202401071
Jie Wang, Shangxi Zhang, Hui Zhang, Yuanyuan Zheng, Lina Liang, Lei Liu
{"title":"Construction of Spiro Systems from Tetrathiafulvalene Derivatives by a Pinacol-like Rearrangement","authors":"Jie Wang, Shangxi Zhang, Hui Zhang, Yuanyuan Zheng, Lina Liang, Lei Liu","doi":"10.1002/ejoc.202401071","DOIUrl":"https://doi.org/10.1002/ejoc.202401071","url":null,"abstract":"An efficient and generalized pinacol-like rearrangement of tetrathiafulvalene (TTF) derivatives has been achieved using 2, 2, 6, 6-tetramethylpiperidine oxide (TEMPO) as a key reagent, in place of a traditional metal catalyst. Examination of numerous TTF derivatives demonstrates the reaction's exceptional tolerance to a variety of substituents, achieving an overall yield of up to 97%. The optimization of reaction conditions and evaluation of reaction applicability were achieved by varying factors such as the redox potential (E11/2) of the substrate molecule, substituent type, substituent position, number of substituents, and structural symmetry. Additionally, the reaction mechanism was explored using isotopic labeling, real-time monitoring UV-Vis absorption spectroscopy, and X-ray diffraction (XRD) analysis. Specifically, TTF is oxidized to TTF+• by p-toluenesulfonic acid (TsOH·H2O). TTF+• subsequently reacts with TEMPO and H2O to form a pinacol-like intermediate, which undergoes a rearrangement to release a 2, 2, 6, 6-tetramethylpiperidin-1-ol (TEMPOH) molecule, forming the rearranged product as a hydrogenated cation, this intermediate undergoes deprotonation, leading to the formation of the final spiro product. This investigation led to the identification of a class of reactions for the efficient conversion of TTF derivatives into their spiro products via pinacol-like rearrangement reaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556328","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Photocatalytic Decarboxylative Fluoroalkylation of α,β-Unsaturated Carboxylic Acids α、β-不饱和羧酸的光催化脱羧氟烷基化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-30 DOI: 10.1002/ejoc.202401144
xiuling Wang, Yaxing Wu, Songlin Xu, hongmei qu, Chao Chen
{"title":"Photocatalytic Decarboxylative Fluoroalkylation of α,β-Unsaturated Carboxylic Acids","authors":"xiuling Wang, Yaxing Wu, Songlin Xu, hongmei qu, Chao Chen","doi":"10.1002/ejoc.202401144","DOIUrl":"https://doi.org/10.1002/ejoc.202401144","url":null,"abstract":"A decarboxylative fluoroalkylation of α,β-unsaturated acids was developed by the use of a dual nickel/photoredox catalysis system. The fluoroalkyl radicals are generated from α-CF3 alkyl bromides by nickel-induced single electron transfer (SET) and are subsequently intercepted by a cinnamic acid to forge the targeted C-C bonds. A wide variety of substrates bearing a diverse set of functional groups were compatible with the mild reaction conditions (visible light, room temperature, cheap metal, no strong oxidant or reductant), thus affording trifluoromethyl analogues of α-methylated allylic compounds.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"492 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541980","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
The Pyramidalization of sp2 Centers in 3/2‐Systems Is a “Structural Breathing” Independent of Energy 3/2 系统中 sp2 中心的金字塔化是与能量无关的 "结构呼吸
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-29 DOI: 10.1002/ejoc.202400623
Henri Brunner, Masahiro Ikeshita, Takashi Tsuno
{"title":"The Pyramidalization of sp2 Centers in 3/2‐Systems Is a “Structural Breathing” Independent of Energy","authors":"Henri Brunner, Masahiro Ikeshita, Takashi Tsuno","doi":"10.1002/ejoc.202400623","DOIUrl":"https://doi.org/10.1002/ejoc.202400623","url":null,"abstract":"In 3/2‐systems, such as the acetate anion H<jats:sub>3</jats:sub>C<jats:sub>α</jats:sub>C′OO<jats:sup>−</jats:sup>, an sp<jats:sup>3</jats:sup> center and an sp<jats:sup>2</jats:sup> center are connected by a covalent bond. The interaction of threefold and twofold symmetry results in the pyramidalization of the sp<jats:sup>2</jats:sup> center during rotation about bond E<jats:sub>sp3</jats:sub>−E<jats:sub>sp2</jats:sub>. Rotation angles <jats:italic>ψ</jats:italic>=0°, ±60°, ±120°, and ±180° account for conformations with a symmetry plane containing the planar sp<jats:sup>2</jats:sup> center C<jats:sub>α</jats:sub>C′OO. However, in all conformations with rotation angles <jats:italic>ψ</jats:italic>≠0°, ±60°, ±120°, and ±180° this symmetry plane is lost and pyramidalization must occur with maxima at rotation angles <jats:italic>ψ</jats:italic>=±30°, ±90°, and ±150°, because the two sides of the sp<jats:sup>2</jats:sup> center C<jats:sub>α</jats:sub>C′OO are different. Inevitably, this leads to a pyramidalization/rotation profile <jats:italic>θ/ψ</jats:italic> with three maxima, three minima, and six zero‐crossings. Thus, myriads of 3/2‐compounds pyramidalize their sp<jats:sup>2</jats:sup> centers each moment to the order of about 2° in a coupled pyramidalization/rotation molecular motion independent of energy.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541392","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Advances in Combined Asymmetric Catalysis of Transition Metal/Phase Transfer Catalysts 过渡金属/相转移催化剂的联合不对称催化研究进展
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-29 DOI: 10.1002/ejoc.202401088
Yi-Fan Dong, Si-Ru Wang, Zhi-Yong Han, Xiang Wu
{"title":"Advances in Combined Asymmetric Catalysis of Transition Metal/Phase Transfer Catalysts","authors":"Yi-Fan Dong, Si-Ru Wang, Zhi-Yong Han, Xiang Wu","doi":"10.1002/ejoc.202401088","DOIUrl":"https://doi.org/10.1002/ejoc.202401088","url":null,"abstract":"Phase-transfer catalysts (PTCs) are chemical agents that facilitate the transfer of molecules or ions between different reaction phases, thereby accelerating heterogeneous reaction processes. Transition metal catalysts are renowned for their versatility in breaking inert chemical bonds and forming new carbon-carbon bonds. Over the past two decades, integrating metal catalysts with phase-transfer catalysts has emerged as a highly valuable and adaptable strategy in modern organic synthesis. This combined catalytic approach highlights the enhanced synthetic capabilities and demonstrates the benefits of merging these two catalytic systems. This review provides an overview of recent advancements in asymmetric catalysis that utilize the synergy between metal and phase-transfer catalysts, focusing on their role in the rapid and efficient synthesis of complex organic molecules with precise stereochemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541910","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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