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Remote C(sp3)–H Carboxylation with CO2 via Visible-Light-Catalyzed 1,5-Hydrogen Atom Transfer
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-13 DOI: 10.1021/acs.orglett.4c04294
Haoran Huang, Xiaoyu Lin, Fanyuanhang Yang, Yuxi Ren, Yuzhen Gao, Weiping Su
{"title":"Remote C(sp3)–H Carboxylation with CO2 via Visible-Light-Catalyzed 1,5-Hydrogen Atom Transfer","authors":"Haoran Huang, Xiaoyu Lin, Fanyuanhang Yang, Yuxi Ren, Yuzhen Gao, Weiping Su","doi":"10.1021/acs.orglett.4c04294","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04294","url":null,"abstract":"The direct carboxylation of C(sp<sup>3</sup>)–H bonds with CO<sub>2</sub> represents a challenging but highly attractive strategy in organic synthesis. In this study, we presented a visible-light-catalyzed strategy for carboxylating remote C(sp<sup>3</sup>)–H bonds with CO<sub>2</sub> via aryl radical induced 1,5-hydrogen atom transfer. This transformation involves generating alkyl radicals via 1,5-hydrogen atom transfer from aryl radicals, forming alkyl carbanions as key intermediates, and a subsequent nucleophilic attack with CO<sub>2</sub>, thereby enabling access to a variety of tertiary and quaternary carboxylic acids in moderate to good yields.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"78 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816485","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
Visible-Light-Enabled Catalytic Intramolecular Double Oxidation of Olefins to ortho-Hydroxylactones
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-13 DOI: 10.1021/acs.orglett.4c03875
Guangxian Chen, Boyi Liu, Lele Zhang, Feiwei Yan, Sanmei Pan, Feiming Li, Zhixiong Cai, Xiaoping Chen, Shunyou Cai
{"title":"Visible-Light-Enabled Catalytic Intramolecular Double Oxidation of Olefins to ortho-Hydroxylactones","authors":"Guangxian Chen, Boyi Liu, Lele Zhang, Feiwei Yan, Sanmei Pan, Feiming Li, Zhixiong Cai, Xiaoping Chen, Shunyou Cai","doi":"10.1021/acs.orglett.4c03875","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03875","url":null,"abstract":"We have effectively utilized cost-effective 2-bromoanthraquinone as a photocatalyst to develop an efficient and environmentally friendly method for producing <i>o</i>-hydroxy lactones under mild visible light irradiation. Importantly, this protocol only relies on oxygen as an oxidant, completely eliminating the need for additional chemical reagents and showcasing a sustainable approach to chemical transformation. Operating at room temperature, we utilized a mixed solvent system of DMF and CHCl<sub>3</sub>, which greatly facilitated the selective conversion of various 2-vinylbenzoic acids and carboxylic acids to functional <i>o</i>-hydroxyl lactones. The process also exhibited excellent diastereoselectivity. Moreover, this versatile strategy is compatible with a wide range of biologically active and complex molecules, offering new opportunities for late-stage structural modifications of these compounds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"200 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816364","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
Dual Inert C-H Bond Site-Selective Activations Enabled by Pd/Norbornene-Mediated Cascade Cyclization toward Medium-Sized Polyheterocyclic Methylene Sulfoximines. 钯/降冰片烯介导的级联环化对中等尺寸多环亚甲基亚磺酰亚胺的双惰性 C-H 键位点选择性活化。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-13 Epub Date: 2024-11-28 DOI: 10.1021/acs.orglett.4c03935
Li Wei, Fang Xun, Xiaojuan Chen, Ting Chen, Zhiyuan Chen
{"title":"Dual Inert C-H Bond Site-Selective Activations Enabled by Pd/Norbornene-Mediated Cascade Cyclization toward Medium-Sized Polyheterocyclic Methylene Sulfoximines.","authors":"Li Wei, Fang Xun, Xiaojuan Chen, Ting Chen, Zhiyuan Chen","doi":"10.1021/acs.orglett.4c03935","DOIUrl":"10.1021/acs.orglett.4c03935","url":null,"abstract":"<p><p>A Pd/norbornene-mediated three-component modular one-step reaction facilitated by dual C-H bond activation and cascade cyclization is reported. This procedure uses norbornene as a catalyst in the Catellani-type reaction and as an alkylating building block to accomplish the dual unactivated C-H bond functionalization protocol, which results in the production of polyheterocyclic eight-membered sulfoximines with an indene-fused moiety. This mild, scalable protocol's wide substrate range makes it ideal for site-selective dual C-H functionalization at the highly chemoselective aryl sites.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"10548-10552"},"PeriodicalIF":4.9,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737811","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
Electrochemical Dichlorinative Cyclization of 1,n-Enynes by 4-Iodotoluene Catalysis. 4-Iodotoluene 催化 1,n-炔的电化学二氯环化反应。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-13 Epub Date: 2024-11-28 DOI: 10.1021/acs.orglett.4c04041
Xu Wang, Longji Li, Zhongjian Du, Xingmin Han, Yang'en You
{"title":"Electrochemical Dichlorinative Cyclization of 1,<i>n</i>-Enynes by 4-Iodotoluene Catalysis.","authors":"Xu Wang, Longji Li, Zhongjian Du, Xingmin Han, Yang'en You","doi":"10.1021/acs.orglett.4c04041","DOIUrl":"10.1021/acs.orglett.4c04041","url":null,"abstract":"<p><p>An electrochemical approach for the indirect oxidative generation of hypervalent iodoarene as a reaction catalyst has been reported. The reaction proceeds first from the generation of active Cl species by electro-oxidation, followed by oxidative transfer to generate ArICl<sub>2</sub>, which subsequently reacts with enynes to achieve cyclization. This protocol provides a simple and green method for accessing dichlorinative cyclization products in high yields with good selectivity.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"10583-10588"},"PeriodicalIF":4.9,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737812","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
HTE-Enabled Development of an Ene-Reductase-Catalyzed Desymmetrization: Remote Control of All-Carbon Quaternary γ-Centers
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-13 DOI: 10.1021/acs.orglett.4c04383
David A. Petrone, Damien Valette, Olivia Boyd, Justin Newman, Erin Plasek, Guangxin Shao, Xiao Wang, Tetsuji Itoh, Matthew Maddess, Feng Peng
{"title":"HTE-Enabled Development of an Ene-Reductase-Catalyzed Desymmetrization: Remote Control of All-Carbon Quaternary γ-Centers","authors":"David A. Petrone, Damien Valette, Olivia Boyd, Justin Newman, Erin Plasek, Guangxin Shao, Xiao Wang, Tetsuji Itoh, Matthew Maddess, Feng Peng","doi":"10.1021/acs.orglett.4c04383","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04383","url":null,"abstract":"We report the remote stereocontrol of all-carbon quaternary γ-centers via an ene-reductase (ERED)-catalyzed desymmetrization of prochiral cyclohexadienones. By leveraging high-throughput experimentation (HTE) protocols, we were able to rapidly identify EREDs capable of desymmetrizing both spirocyclic cyclohexadienones and non-spirocyclic 2,6-disubstituted cyclohexadienone substrates in up to 85% yield with excellent levels of stereoselectivity (up to &gt;99% ee and &gt;20:1 dr) under mild reaction conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816487","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
Protecting-Group Free Total Synthesis of β-Levantenolide through Late Stage Bromo-Spirocyclization. 通过后期溴螺环化无保护基团全合成β-莱万特内酯
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-13 Epub Date: 2024-11-28 DOI: 10.1021/acs.orglett.4c03542
Saubhik Ghosh, Shrestha Chatterjee, Samik Nanda
{"title":"Protecting-Group Free Total Synthesis of β-Levantenolide through Late Stage Bromo-Spirocyclization.","authors":"Saubhik Ghosh, Shrestha Chatterjee, Samik Nanda","doi":"10.1021/acs.orglett.4c03542","DOIUrl":"10.1021/acs.orglett.4c03542","url":null,"abstract":"<p><p>We describe a concise asymmetric total synthesis of naturally occurring [5,5]-oxaspirolactone β-levantenolide through an adventitious bromo-spirocyclization reaction of a <i>trans</i>-decalin appended γ-alkylidenebutenolide. The γ-alkylidenebutenolide core was constructed through \"Pd-Cu\" bimetallic cascade lactonization reaction of properly functionalized enantiopure alkyne. (+)-Sclareolide was used as a chiral pool starting material to access the desired alkyne.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"10453-10457"},"PeriodicalIF":4.9,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737814","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 Primary and Secondary Amines via Electrochemical Reduction of Hydrazines
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-13 DOI: 10.1021/acs.orglett.4c04040
Dong Wang, Qiulu Wang, Mingxia Liu, Zihan Liu, Zixuan Wang, Wenhui Ji, Yu Wang, Jin Wang
{"title":"Synthesis of Primary and Secondary Amines via Electrochemical Reduction of Hydrazines","authors":"Dong Wang, Qiulu Wang, Mingxia Liu, Zihan Liu, Zixuan Wang, Wenhui Ji, Yu Wang, Jin Wang","doi":"10.1021/acs.orglett.4c04040","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04040","url":null,"abstract":"We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- and 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope of primary and secondary amines in high yields. The mechanistic investigation suggests that the amine product is formed by consecutive SET reduction, and utilization of a hydrazine HCl salt is important for providing sufficient conductivity and acidity to facilitate this reaction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"91 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816365","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
Metal-Catalyzed Hydrogen Atom Transfer (MHAT) Hydroalkylation with Electron-Deficient Alkynes. 金属催化氢原子转移 (MHAT) 与缺电子炔烃的氢烷基化反应。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-13 Epub Date: 2024-11-28 DOI: 10.1021/acs.orglett.4c03943
Laura G Rodríguez, Josep Bonjoch, Ben Bradshaw
{"title":"Metal-Catalyzed Hydrogen Atom Transfer (MHAT) Hydroalkylation with Electron-Deficient Alkynes.","authors":"Laura G Rodríguez, Josep Bonjoch, Ben Bradshaw","doi":"10.1021/acs.orglett.4c03943","DOIUrl":"10.1021/acs.orglett.4c03943","url":null,"abstract":"<p><p>We present a novel strategy for olefin construction via the reductive coupling of electron-neutral alkenes with electron-deficient alkynes under metal-catalyzed hydrogen atom transfer conditions. This methodology provides selective access to both <i>trans</i> and the more challenging-to-synthesize <i>cis</i> isomers and permits the olefin to be installed next to sterically hindered centers, key factors in the synthesis of biologically active compounds. The reaction exhibits broad functional group tolerance and proceeds under mild, nontoxic conditions with high atom efficiency.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"10553-10558"},"PeriodicalIF":4.9,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737813","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
Remote Alkynylation of Aliphatic Amines. 脂肪胺的远程炔化。
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-13 Epub Date: 2024-11-27 DOI: 10.1021/acs.orglett.4c03468
Elizabeth M Dauncey, Tom D Sheppard, Peter D Smith, Rachel H Munday
{"title":"Remote Alkynylation of Aliphatic Amines.","authors":"Elizabeth M Dauncey, Tom D Sheppard, Peter D Smith, Rachel H Munday","doi":"10.1021/acs.orglett.4c03468","DOIUrl":"10.1021/acs.orglett.4c03468","url":null,"abstract":"<p><p>Advancements in transition metal catalyzed C-H activation/functionalization cascades have allowed the synthetic chemist's toolbox to be significantly expanded. Despite this, protocols for the remote alkynylation of linear aliphatic amines still remain limited. Herein, a palladium-catalyzed directing-group approach to alkynylation of aliphatic amines is disclosed. The synthetic utility was demonstrated with a gram-scale reaction and a functional group compatibility test.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"10441-10446"},"PeriodicalIF":4.9,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737815","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
Copper-Catalyzed Cycloaddition/Coupling Cascades of Azomethine Imines with Alkynes for Divergent Synthesis of (Z)-Alkenyl and Alkynyl N,N′-Bicyclic Pyrazolidinones
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-12 DOI: 10.1021/acs.orglett.4c03824
Wei Jiang, Bo-Xun Sun, Tai-Gang Fan, Cui Zhang, Xin-Song Zhou, Yuehai Shen, Ya-Min Li
{"title":"Copper-Catalyzed Cycloaddition/Coupling Cascades of Azomethine Imines with Alkynes for Divergent Synthesis of (Z)-Alkenyl and Alkynyl N,N′-Bicyclic Pyrazolidinones","authors":"Wei Jiang, Bo-Xun Sun, Tai-Gang Fan, Cui Zhang, Xin-Song Zhou, Yuehai Shen, Ya-Min Li","doi":"10.1021/acs.orglett.4c03824","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03824","url":null,"abstract":"Copper-catalyzed cycloaddition/coupling cascades utilizing azomethine imines and alkynes have been developed for the divergent synthesis of (<i>Z</i>)-alkenyl and alkynyl <i>N</i>,<i>N′</i>-bicyclic pyrazolidinones by varying the reaction conditions. The choice of inert or oxidative atmosphere plays a crucial role in determining the transformation pathways. These reactions have broad substrate scopes and mild conditions, making them potentially useful.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"87 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810000","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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