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From benzopyrroles to phenylpyrroles: remodeling of indoles enabled by photoredox catalysis† 从苯并吡咯到苯基吡咯：光氧化还原催化实现吲哚的重塑†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00505d
Wei Xu , Bin Cheng , Yaoge Zhang , Lijing Fang , Hongbin Zhai , Cuiping Wang , Taimin Wang
{"title":"From benzopyrroles to phenylpyrroles: remodeling of indoles enabled by photoredox catalysis†","authors":"Wei Xu ,&nbsp;Bin Cheng ,&nbsp;Yaoge Zhang ,&nbsp;Lijing Fang ,&nbsp;Hongbin Zhai ,&nbsp;Cuiping Wang ,&nbsp;Taimin Wang","doi":"10.1039/d3qo00505d","DOIUrl":"10.1039/d3qo00505d","url":null,"abstract":"<div><p>A facile approach toward 3-(<em>o</em>-aminophenyl)pyrroles was developed by remodeling of <em>N</em>-sulfonyl-3-acyl indoles with <em>N</em>-phenylglycines under photoredox catalysis. This strategy enables the conversion of a fused bicyclic system into a biaryl scaffold, mechanically involving a Giese-type radical addition to C2<img>C3, C2–N cleavage of the resulting indoline skeleton, and generation of a new pyrrole motif. This novel methodology provides an innovative strategy for the synthesis of potentially valuable 3-(<em>o</em>-aminophenyl)pyrroles and related alkaloids.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3875-3882"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3865633","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Binaphthyl-derived armchair-type molecular carbon rings with chirality: synthesis and optical properties† 具有手性的联萘衍生扶手椅型分子碳环：合成和光学性质†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01977a
Qiang Huang , Jinling Zhang , Huafeng Chen , Xin Kong , Peng Xu , Pingwu Du
{"title":"Binaphthyl-derived armchair-type molecular carbon rings with chirality: synthesis and optical properties†","authors":"Qiang Huang ,&nbsp;Jinling Zhang ,&nbsp;Huafeng Chen ,&nbsp;Xin Kong ,&nbsp;Peng Xu ,&nbsp;Pingwu Du","doi":"10.1039/d2qo01977a","DOIUrl":"10.1039/d2qo01977a","url":null,"abstract":"<div><p>Herein, we report the synthesis of binaphthyl-derived hoop-shaped aromatic hydrocarbon enantiomers (<strong>RCR</strong> and <strong>SCR</strong>) as the segments of (9,9) armchair CNTs. After the structures were identified by HR-MS (MALDI-TOF) and NMR spectroscopy, further circular dichroism (CD) analysis confirmed their chirality. Unlike most of the previously reported chiral-type CNT segments in which chirality arises from the absence of a plane of symmetry or an inversion center in the molecule, the chirality for <strong>RCR</strong> and <strong>SCR</strong> is assigned to the introduction of foreign chiral sources, namely, oxyethyl-modified binaphthyl units. Finally, their photophysical properties were also investigated by absorption and fluorescence spectroscopies.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 4","pages":"Pages 911-915"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3866329","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemo- and regioselective synthesis of C3-sulfonate esters and C4-chlorides of quinolines under metal-free conditions† 在无金属条件下化学和区域选择性合成喹啉的C3磺酸盐和C4氯化物†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01621d
Dong Chen , Yan Liu , Zhiqiang Lu , Haojie Wang , Mingjia Li , Dan Yue , Zhenling Wang
{"title":"Chemo- and regioselective synthesis of C3-sulfonate esters and C4-chlorides of quinolines under metal-free conditions†","authors":"Dong Chen ,&nbsp;Yan Liu ,&nbsp;Zhiqiang Lu ,&nbsp;Haojie Wang ,&nbsp;Mingjia Li ,&nbsp;Dan Yue ,&nbsp;Zhenling Wang","doi":"10.1039/d2qo01621d","DOIUrl":"10.1039/d2qo01621d","url":null,"abstract":"<div><p>Disclosed herein is a novel one-pot synthesis of C3-sulfonate esters and C4-chlorides of quinolines from quinoline <em>N</em>-oxides with sulfonyl chloride. Sulfonyl chlorides were used in two roles, namely sulfonylation and chlorination. Both arenesulfonyl chlorides and aliphatic sulfonyl chlorides were found to be suitable precursors for sulfonation and chlorination reagents. Therefore, a wide variety of C3-sulfonate esters and C4-chlorides of quinolines were afforded under metal-free conditions. This procedure features practicality, high efficiency, environmental friendliness and atomic economy.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 4","pages":"Pages 936-942"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3866334","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A general protocol for stereoselective construction of enaminyl sulfonyl fluorides† 烯甲酰基磺酰基氟化物立体选择性构建的通用方案†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01810a
Liu-Yang Chen , K.P. Rakesh , Hua-Li Qin
{"title":"A general protocol for stereoselective construction of enaminyl sulfonyl fluorides†","authors":"Liu-Yang Chen ,&nbsp;K.P. Rakesh ,&nbsp;Hua-Li Qin","doi":"10.1039/d2qo01810a","DOIUrl":"10.1039/d2qo01810a","url":null,"abstract":"<div><p>A simple, efficient, and mild reaction of 2-chloroprop-2-ene-1-sulfonyl fluoride (CESF) with amines was developed, affording a variety of highly functionalized enaminyl sulfonyl fluorides in good to excellent yields (56–96%). This transformation features a broad substrate scope, high atom economy, operational simplicity and up to 100% stereoselectivity, which can provide great application value in medicinal chemistry, chemical biology, and drug discovery.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 4","pages":"Pages 951-956"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3866336","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Copper-catalyzed dearomative 1,4-carboxylate rearrangement of 2-carbonateindoles† 铜催化2-羰基吲哚的1,4-羧酸酯脱芳重排†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01647h
Yan Zhu , Ying Shao , Shengbiao Tang , Jiangtao Sun
{"title":"Copper-catalyzed dearomative 1,4-carboxylate rearrangement of 2-carbonateindoles†","authors":"Yan Zhu ,&nbsp;Ying Shao ,&nbsp;Shengbiao Tang ,&nbsp;Jiangtao Sun","doi":"10.1039/d2qo01647h","DOIUrl":"10.1039/d2qo01647h","url":null,"abstract":"<div><p>A novel dearomative 1,4-rearrangement reaction of 2-carbonateindoles with aryl diazoacetates has been developed in the presence of a copper catalyst, which might proceed through a tandem formation of a zwitterionic intermediate, intramolecular cyclization and ring-opening reaction to give the final rearrangement products containing an all-carbon quaternary center with two newly formed C–C bonds. In this sequence, the disruption of the aromaticity of indole has been realized, associated with 1,4-carboxylate rearrangements.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 1","pages":"Pages 99-103"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3866342","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photocatalyst-free, metal-free, visible light-induced thiolation/pyridylation of styrenes using an electron donor–acceptor complex as a bifunctional reagent† 无光催化剂，无金属，可见光诱导苯乙烯硫基化/吡啶化使用电子供体-受体配合物作为双功能试剂†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01889f
Jiaxuan Shen , Jincan Li , Meijun Chen , Yimin Chen
{"title":"Photocatalyst-free, metal-free, visible light-induced thiolation/pyridylation of styrenes using an electron donor–acceptor complex as a bifunctional reagent†","authors":"Jiaxuan Shen ,&nbsp;Jincan Li ,&nbsp;Meijun Chen ,&nbsp;Yimin Chen","doi":"10.1039/d2qo01889f","DOIUrl":"10.1039/d2qo01889f","url":null,"abstract":"<div><p>Herein, we report a visible light-induced photocatalytic protocol for the thiolation and pyridylation of styenes using a thiolate-based EDA complex as a bifunctional reagent. The reaction occurrs under mild conditions free of a photocatalyst, metal or external redox agent, possessing a broad substrate scope. The protocol can be practiced on the gram-scale, and late-stage functionalization of natural product- and drug-derived complex molecules is also possible.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 5","pages":"Pages 1166-1172"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934859","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 photoinduced alkylative [3 + 2] annulation of terminal alkynes with N-alkyl isoquinolin-2-iums by catalytic isoquinoline-based electron donor–acceptor complex† 基于异喹啉的电子供体-受体络合物催化n-烷基异喹啉-2-末端炔的无金属光诱导[3 + 2]环化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01754g
Ya-Fei Han , Yang Li , Xuan-Hui Ouyang , Ming Hu , Jing-Hao Qin , Ze Tan , Jin-Heng Li
{"title":"Metal-free photoinduced alkylative [3 + 2] annulation of terminal alkynes with N-alkyl isoquinolin-2-iums by catalytic isoquinoline-based electron donor–acceptor complex†","authors":"Ya-Fei Han ,&nbsp;Yang Li ,&nbsp;Xuan-Hui Ouyang ,&nbsp;Ming Hu ,&nbsp;Jing-Hao Qin ,&nbsp;Ze Tan ,&nbsp;Jin-Heng Li","doi":"10.1039/d2qo01754g","DOIUrl":"10.1039/d2qo01754g","url":null,"abstract":"<div><p>A new, metal-free electron donor–acceptor (EDA) complex photocatalysis strategy for alkylative [3 + 2] annulation of <em>N</em>-alkyl isoquinolin-2-ium salts with common alkynes in ethyl actate/H<sub>2</sub>O to assemble highly functionalized pyrrolo[2,1-<em>a</em>]isoquinolines is presented. Upon photoinducing reactivity using the catalytic isoquinoline-based EDA complex, this method enables incorporation of alkynes as two-carbon units to achieve alkylative [3 + 2] annulation of <em>N</em>-alkyl isoquinolin-2-ium salts, and is notable for its excellent site selectivity, tolerance of a wide range of functional groups, the use of aqueous media and avoidance of the need for expensive external photocatalysts and basic or acidic promotors. Mechanistic study indicates that the EDA complex is generated from association of a catalytic isoquinoline with <em>N</em>-alkyl isoquinolin-2-ium salts to photoinduce reactivity.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 5","pages":"Pages 1173-1181"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934860","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 cyclopenta[b]benzofurans via biomimetic oxidative phenol–enamine [3 + 2] cycloaddition† 仿生氧化苯酚- enamine[3 + 2]环加成法合成环五[b]苯并呋喃
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01916g
Muhammad Adnan Bashir , Xuanjie Chen , Tie Wang , Hui Guo , Hongbin Zhai
{"title":"Synthesis of cyclopenta[b]benzofurans via biomimetic oxidative phenol–enamine [3 + 2] cycloaddition†","authors":"Muhammad Adnan Bashir ,&nbsp;Xuanjie Chen ,&nbsp;Tie Wang ,&nbsp;Hui Guo ,&nbsp;Hongbin Zhai","doi":"10.1039/d2qo01916g","DOIUrl":"10.1039/d2qo01916g","url":null,"abstract":"<div><p>A hemin/<em>t</em>-BuOOH-catalyzed oxidative phenol–enamine formal [3 + 2] cycloaddition has been developed, enabling the environmentally benign synthesis of valuable cyclopenta[<em>b</em>]benzofuran scaffolds under sustainable reaction conditions with excellent atom- and step-economy. Mechanistic studies point to the involvement of a two-electron oxidation pathway. Based on the preliminary biological investigations, compound <strong>3ay</strong> displayed moderate anti-cancer activities (IC<sub>50</sub> = 27.73 μM) against MCF7 cells (breast cancer cells).</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 5","pages":"Pages 1213-1218"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934865","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cu-catalysed three-component C–H trifluoroalkylation of glycine derivatives: access to diverse CF3-containing amino acids† cu催化的甘氨酸衍生物的三组分C-H三氟烷基化:获取多种含cf3的氨基酸†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00267e
Yadong Li , Dengfu Lu , Yuefa Gong
{"title":"Cu-catalysed three-component C–H trifluoroalkylation of glycine derivatives: access to diverse CF3-containing amino acids†","authors":"Yadong Li ,&nbsp;Dengfu Lu ,&nbsp;Yuefa Gong","doi":"10.1039/d3qo00267e","DOIUrl":"10.1039/d3qo00267e","url":null,"abstract":"<div><p>A Cu-catalysed method that selectively incorporates a trifluoromethyl group and an alkene moiety onto the α carbon of glycine derivatives has been developed using commercialized Togni II reagent. In this three-component reaction, both the N-protecting group of glycinates and the Cu ligand played critical roles in controlling the catalytic activity and chemo-selectivity. Under the optimized conditions, a variety of unactivated alkenes were successively trifluoromethylated and coupled with <em>N</em>-PMP glycine derivatives, providing facile access to structurally diverse CF<sub>3</sub>-containing amino acids, as well as functionalized peptides. In addition, this protocol also demonstrated potential application in the ligation between an alkene-tagged functional molecule and a peptide with a glycine N-terminus.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2301-2309"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934878","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Iron-mediated divergent reductive coupling reactions of heteroarenes with alkenes† 铁介导的杂环芳烃与烯烃†的发散还原偶联反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01985j
Cong Zhang , Yuhang He , Guanghui An
{"title":"Iron-mediated divergent reductive coupling reactions of heteroarenes with alkenes†","authors":"Cong Zhang ,&nbsp;Yuhang He ,&nbsp;Guanghui An","doi":"10.1039/d2qo01985j","DOIUrl":"10.1039/d2qo01985j","url":null,"abstract":"<div><p>Iron-mediated divergent reductive coupling reactions of heteroarenes with alkenes have been developed. By switching the substituent site at the C2 and C4 positions of quinolines, either C2 Minisci alkylation or C4 reductive alkylation could be achieved. These approaches feature mild conditions and sensitive functional group tolerance, which enables the functionalization of natural products and medicines. Mechanism investigation revealed that Fe(dibm)<sub>3</sub> would be a dual promoter for both alkyl radical transfer and generation of the more reactive hydrogen donor Ph(RO)SiH<sub>2.</sub></p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2318-2323"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934880","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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