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Synthesis of 12- to 26-Membered Macrocyclic Dienes by Directed Intramolecular Alkene/Alkyne Cross-Coupling
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c0110610.1021/acs.orglett.5c01106
Xiandie Zhang, Xiuying Liu, Xiaoli Li, Yini Wang, Rui He, Guofu Zhong* and Jian Zhang*, 
{"title":"Synthesis of 12- to 26-Membered Macrocyclic Dienes by Directed Intramolecular Alkene/Alkyne Cross-Coupling","authors":"Xiandie Zhang,&nbsp;Xiuying Liu,&nbsp;Xiaoli Li,&nbsp;Yini Wang,&nbsp;Rui He,&nbsp;Guofu Zhong* and Jian Zhang*,&nbsp;","doi":"10.1021/acs.orglett.5c0110610.1021/acs.orglett.5c01106","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01106https://doi.org/10.1021/acs.orglett.5c01106","url":null,"abstract":"<p >The first iridium-catalyzed intramolecular alkene/alkyne cross-coupling reaction has been developed to prepare a wide range of 12- to 26-membered macrocyclic 1,3-dienes. This operationally simple protocol proceeded by NHTs amide-enabled alkenyl C–H functionalization and exhibited wide functionality tolerance and excellent <i>E/Z</i> ratio selectivity.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 15","pages":"4074–4078 4074–4078"},"PeriodicalIF":4.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842166","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Trifluoromethylated Alkenes via a Tandem Aldol/N-Acyloxyphthalimide-Assisted Decarboxylation Sequence
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c0060110.1021/acs.orglett.5c00601
Fei Huang, Yunquan Man and Bo Xu*, 
{"title":"Synthesis of Trifluoromethylated Alkenes via a Tandem Aldol/N-Acyloxyphthalimide-Assisted Decarboxylation Sequence","authors":"Fei Huang,&nbsp;Yunquan Man and Bo Xu*,&nbsp;","doi":"10.1021/acs.orglett.5c0060110.1021/acs.orglett.5c00601","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00601https://doi.org/10.1021/acs.orglett.5c00601","url":null,"abstract":"<p >We have developed a metal-free approach for synthesizing <i>E</i>-trifluoromethylated alkenes from readily available aldehydes and the <i>N</i>-hydroxyphtalimide ester of trifluoropropionic acid. To address the challenge of defluorination, we conducted high-throughput screening of reaction conditions. We discovered that acid–base co-catalysis effectively suppresses defluorination, thereby enhancing product yields. A key advantage of our method is its reliance on inexpensive, commercially available starting materials and straightforward reaction conditions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 15","pages":"3889–3892 3889–3892"},"PeriodicalIF":4.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842498","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
2D Aza-COF-Supported Ruthenium Complex: A Recyclable Auto-Tandem Catalyst for the Preparation of Quinazolinones from Allylic Alcohols and o-Aminobenzamides
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c00529
Xiaozhong Chen, Yong Xu, Wei Zhao, Xiaoting Wang, Qixun Shi, Shouhai Zhang, Feng Li
{"title":"2D Aza-COF-Supported Ruthenium Complex: A Recyclable Auto-Tandem Catalyst for the Preparation of Quinazolinones from Allylic Alcohols and o-Aminobenzamides","authors":"Xiaozhong Chen, Yong Xu, Wei Zhao, Xiaoting Wang, Qixun Shi, Shouhai Zhang, Feng Li","doi":"10.1021/acs.orglett.5c00529","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00529","url":null,"abstract":"Ruthenium complex Ru(<i>p-</i>cymene)@Aza-COF was synthesized by the immobilization of [Ru(<i>p-</i>cymene)Cl][Cl] on a 2D Aza-COF. Then, this complex was utilized as an auto-tandem catalyst for the preparation of quinazolinones from allylic alcohols and <i>o</i>-aminobenzamides via redox isomerization/acceptorless dehydrogenative coupling. More importantly, its catalytic activity is well maintained during six runs.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143806152","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Domino-Annulation-Based Approach to Synthesize Bridged Bis-thiopyrano[2,3-b]indoles and Unbridged Thiopyrano[2,3-b]indoles
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c00652
Yan-Hui Fu, Chun Zhang, Wei Xu, Wenting Fu, Wenjun Zhang, Kang Zhou, Hongbin Zhai, Taimin Wang, Bin Cheng
{"title":"Domino-Annulation-Based Approach to Synthesize Bridged Bis-thiopyrano[2,3-b]indoles and Unbridged Thiopyrano[2,3-b]indoles","authors":"Yan-Hui Fu, Chun Zhang, Wei Xu, Wenting Fu, Wenjun Zhang, Kang Zhou, Hongbin Zhai, Taimin Wang, Bin Cheng","doi":"10.1021/acs.orglett.5c00652","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00652","url":null,"abstract":"A novel domino strategy for the construction of intricate bridged bis-thiopyrano[2,3-<i>b</i>]indoles was disclosed, which involved one molecule of 3-formylchromones and two molecules of indoline-2-thiones, enabling the formation of four new bonds in a single operation. The transformation occurred under mild reaction conditions, facilitated by the synergistic action of the base NaHCO<sub>3</sub> and the catalytic acid ZnCl<sub>2</sub>. Notably, when these bridged bis-thiopyrano[2,3-<i>b</i>]indole skeletons were treated with alkyl halides under basic conditions, they underwent deconstruction to yield alkylthio-substituted indole-decorated thiopyrano[2,3-<i>b</i>]indoles.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"5 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143806153","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Rh(III)-Catalyzed Indole Dearomative 1,2-Alkoxyl Shift Rearrangement
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c0105110.1021/acs.orglett.5c01051
Can Yang, Lixing Shen, Ying Xie, Jianzhang Li*, Huanfeng Jiang and Wei Zeng*, 
{"title":"Rh(III)-Catalyzed Indole Dearomative 1,2-Alkoxyl Shift Rearrangement","authors":"Can Yang,&nbsp;Lixing Shen,&nbsp;Ying Xie,&nbsp;Jianzhang Li*,&nbsp;Huanfeng Jiang and Wei Zeng*,&nbsp;","doi":"10.1021/acs.orglett.5c0105110.1021/acs.orglett.5c01051","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01051https://doi.org/10.1021/acs.orglett.5c01051","url":null,"abstract":"<p >A Rh(III)-catalyzed dearomative C3 alkoxylation of indoles via cascade C(sp<sup>2</sup>)–H activation and 1,2-alkoxyl shift rearrangement has been developed. This method provides an efficient strategy to rapidly assemble 3-alkoxyindolin-2-one scaffolds using alcohols as alkoxyl sources. Mechanistic studies indicate that indolyl C2 alkoxylation followed by Ag(I)/Cu(II)-mediated 1,2-alkoxyl migration is involved in this transformation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 15","pages":"4052–4056 4052–4056"},"PeriodicalIF":4.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842168","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Ether-Directed Enantioselective C(sp2)–H Borylation for the Synthesis of Axially Chiral Biaryls 以醚为导向的对映体选择性 C(sp2)-H Borylation 技术合成轴向手性双环化合物
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c00919
Changji Liu, Chengcai Xia, Shu-Yong Song, Senmiao Xu
{"title":"Ether-Directed Enantioselective C(sp2)–H Borylation for the Synthesis of Axially Chiral Biaryls","authors":"Changji Liu, Chengcai Xia, Shu-Yong Song, Senmiao Xu","doi":"10.1021/acs.orglett.5c00919","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00919","url":null,"abstract":"We report an ether-directed enantioselective C(sp<sup>2</sup>)–H borylation catalyzed by a chiral bidentate boryl ligand (CBL)/iridium system for constructing axially chiral biaryls. This method delivered diverse chiral biaryls with good to high enantioselectivities, accommodating varied electronic and steric substituents on the aryl rings. Gram-scale synthesis and downstream transformations of the C–B bond underscored its practicality.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"21 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813973","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
1,2-Dichloroethane as a Gaseous Acetylene Source for the Rapid Assembly of Isoquinolino[1,2-b]quinazolinone Scaffolds
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c00925
Xinxin Zhu, Mengyao Shi, Cuilian Xu, Xiaoping Xue, Lijun Zhang, Liangxin Fan
{"title":"1,2-Dichloroethane as a Gaseous Acetylene Source for the Rapid Assembly of Isoquinolino[1,2-b]quinazolinone Scaffolds","authors":"Xinxin Zhu, Mengyao Shi, Cuilian Xu, Xiaoping Xue, Lijun Zhang, Liangxin Fan","doi":"10.1021/acs.orglett.5c00925","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00925","url":null,"abstract":"Reported herein is a novel ruthenium(II)-catalyzed [4 + 2] annulation of quinazolinones with 1,2-dichloroethane (DCE), resulting in a myriad of isoquinolino[1,2-<i>b</i>]quinazolinone scaffolds. In this protocol, DCE serves not only as a solvent but also as an acetylene source. The fused quinazolinones undergo versatile transformations and provide a rapid and convenient way to access several important bioactive molecule analogues such as Rutecarpine, Euxylophoricine B and Euxylophoricine E. The potential reaction pathway was elucidated through detailed mechanistic studies and Density Functional Theory (DFT) calculations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"16 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143806155","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Nickel-Catalyzed Electroreductive Heck Reaction: A Divergent Synthesis of C7- or C2-Arylindolines
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c0049510.1021/acs.orglett.5c00495
Yongjie Yang, Balati Hasimujiang, Zaimu Cao, Qingbin Yuan, Xinwei Hu* and Zhixiong Ruan*, 
{"title":"Nickel-Catalyzed Electroreductive Heck Reaction: A Divergent Synthesis of C7- or C2-Arylindolines","authors":"Yongjie Yang,&nbsp;Balati Hasimujiang,&nbsp;Zaimu Cao,&nbsp;Qingbin Yuan,&nbsp;Xinwei Hu* and Zhixiong Ruan*,&nbsp;","doi":"10.1021/acs.orglett.5c0049510.1021/acs.orglett.5c00495","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00495https://doi.org/10.1021/acs.orglett.5c00495","url":null,"abstract":"<p >Herein, we present a novel electrochemically driven nickel-catalyzed Heck reaction of readily available <i>N</i>-arylacrylindoles for the construction of both 7-arylindolines and 2-arylindolines. The reaction proceeds in an undivided electrochemical cell and employs a sacrificial zinc anode as the reductant. This catalytic protocol features a consecutive electroreductive process under exceedingly mild reaction conditions, with moderate yields. Detailed mechanistic studies indicate that the reaction involves a domino sequence of intramolecular electroreductive Heck arylation and selective C–C or C–O bond cleavage, which could be accomplished by aryl migration or carbethoxy removal.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 15","pages":"3838–3843 3838–3843"},"PeriodicalIF":4.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842248","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Fused-Housane Derivatives via Intramolecular [2 + 2] Photocycloaddition
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c0046810.1021/acs.orglett.5c00468
David Suárez-García, Miguel A. Rodríguez, Iratxe Barbolla and Rubén Vicente*, 
{"title":"Synthesis of Fused-Housane Derivatives via Intramolecular [2 + 2] Photocycloaddition","authors":"David Suárez-García,&nbsp;Miguel A. Rodríguez,&nbsp;Iratxe Barbolla and Rubén Vicente*,&nbsp;","doi":"10.1021/acs.orglett.5c0046810.1021/acs.orglett.5c00468","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00468https://doi.org/10.1021/acs.orglett.5c00468","url":null,"abstract":"<p >Herein, we describe a [2 + 2] photocycloaddition of cyclopropenes bearing a styryl group to prepare housane derivatives. The reaction occurs via selective excitation of the styrene fragment, enabling a completely stereoselective stepwise [2 + 2] cycloaddition. Fused-housane derivatives with an unprecedented substitution pattern are prepared in a simple manner using convenient visible light.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 15","pages":"3825–3830 3825–3830"},"PeriodicalIF":4.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143842494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 12- to 26-Membered Macrocyclic Dienes by Directed Intramolecular Alkene/Alkyne Cross-Coupling
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-09 DOI: 10.1021/acs.orglett.5c01106
Xiandie Zhang, Xiuying Liu, Xiaoli Li, Yini Wang, Rui He, Guofu Zhong, Jian Zhang
{"title":"Synthesis of 12- to 26-Membered Macrocyclic Dienes by Directed Intramolecular Alkene/Alkyne Cross-Coupling","authors":"Xiandie Zhang, Xiuying Liu, Xiaoli Li, Yini Wang, Rui He, Guofu Zhong, Jian Zhang","doi":"10.1021/acs.orglett.5c01106","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01106","url":null,"abstract":"The first iridium-catalyzed intramolecular alkene/alkyne cross-coupling reaction has been developed to prepare a wide range of 12- to 26-membered macrocyclic 1,3-dienes. This operationally simple protocol proceeded by NHTs amide-enabled alkenyl C–H functionalization and exhibited wide functionality tolerance and excellent <i>E/Z</i> ratio selectivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"108 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143806146","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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