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Palladium-Catalyzed Fluorinated Olefination of Aromatics
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04254
Xin Liu, Yalong Li, Yilian Song, Jingyi Guo, Zechao Liu, Yingsheng Zhao
{"title":"Palladium-Catalyzed Fluorinated Olefination of Aromatics","authors":"Xin Liu, Yalong Li, Yilian Song, Jingyi Guo, Zechao Liu, Yingsheng Zhao","doi":"10.1021/acs.orglett.4c04254","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04254","url":null,"abstract":"Palladium-mediated, ligand-promoted C–H fluorinated olefination of aromatic derivatives is reported employing 2-bromo-3,3,3-trifluoropropene (BTP) as the fluorinating reagent. Bioactive compounds, such as Isatin, exhibited excellent compatibility with this reaction, underscoring the significance of this methodology for the synthesis of important derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"82 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832720","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
Intramolecular Anti-Markovnikov Alkene Hydroaminative Cyclization to cis-2,3-Disubstituted Piperidines 分子内反马尔科夫尼科夫烯烃氢化氨基环化成顺式-2,3-二取代哌啶类化合物
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04345
Shaoyu Hao, Lin Tang, Chaoren Shen, Kaiwu Dong
{"title":"Intramolecular Anti-Markovnikov Alkene Hydroaminative Cyclization to cis-2,3-Disubstituted Piperidines","authors":"Shaoyu Hao, Lin Tang, Chaoren Shen, Kaiwu Dong","doi":"10.1021/acs.orglett.4c04345","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04345","url":null,"abstract":"Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a (<i>Z</i>)/(<i>E</i>)-isomeric mixture of trisubstituted alkenes using the lactate-derived <i>C</i><sub>2</sub>-symmetric arylthiol catalyst was developed for the synthesis of <i>cis</i>-2,3-disubstituted piperidines and azepane in high diastereoselectivity and good yields. The origin of diastereoselectivity and the observed different hydroamination rate of alkene with different configurations were elucidated by the experimental and computational investigation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"17 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833017","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
The Synthesis of Sulfonyl Fluoride Functionalized 2-Aminothiazoles Using a Diversity Oriented Clicking Strategy
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04393
Joshua W. Kop, Carol Hua, Daniel L. Priebbenow, Christopher J. Smedley
{"title":"The Synthesis of Sulfonyl Fluoride Functionalized 2-Aminothiazoles Using a Diversity Oriented Clicking Strategy","authors":"Joshua W. Kop, Carol Hua, Daniel L. Priebbenow, Christopher J. Smedley","doi":"10.1021/acs.orglett.4c04393","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04393","url":null,"abstract":"We present a Diversity Oriented Clicking approach to synthesize a library of novel clickable <i>N</i>-substituted 2-aminothiazoles which serve as versatile hubs for SuFEx click chemistry diversification. Leveraging the spring-loaded reactivity of the 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) connectors, the transformation is simple to perform, tolerant of a wide range of functionality, and regioselective for a single product. Finally, we propose a detailed stepwise reaction mechanism that is supported by experimental and computational analysis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"67 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833057","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
Staudinger Cleavages of Amides on Naphthalene for the Ipsilateral Effect of 1,8-Substituents 萘上酰胺的施陶丁格裂解作用对 1，8-取代基的同位效应的影响
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04337
Lunyu Ou, Zhengyi Yi, Yue Zhang, Yufen Zhao, Hua Fu
{"title":"Staudinger Cleavages of Amides on Naphthalene for the Ipsilateral Effect of 1,8-Substituents","authors":"Lunyu Ou, Zhengyi Yi, Yue Zhang, Yufen Zhao, Hua Fu","doi":"10.1021/acs.orglett.4c04337","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04337","url":null,"abstract":"8-(Azidomethyl)-1-naphthoic acid was elaborately prepared, and its coupling with amines provided the corresponding 8-(azidomethyl)-1-naphthamides. The Staudinger reactions of 8-(azidomethyl)-1-naphthamides with phosphine produced iminophosphoranes, and easy intramolecular cyclization of the iminophosphoranes afforded 2,3-dihydro-1<i>H</i>-benzo[<i>de</i>]isoquinolin-1-one leaving amines with almost quantitative conversion rates for the ipsilateral effect of 1,8-substituents on naphthalene. The protocol exhibits some advantages, including a readily available protecting group, cleavages of amides in almost quantitative conversion rates, an aqueous medium, reactions at room temperature, a broad substrate scope, wide functional group tolerance, and suitable scale-up reactions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"5 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833016","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 an Isomerized Bithiazole Imide (iBTzI) Acceptor and π-Extension via Intramolecular Noncovalent Interactions 通过分子内非共价相互作用合成异构化双噻唑酰亚胺 (iBTzI) 受体并进行 π 延伸
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04205
Lanen Wei, Kunhan Xu, Ting Qi
{"title":"Synthesis of an Isomerized Bithiazole Imide (iBTzI) Acceptor and π-Extension via Intramolecular Noncovalent Interactions","authors":"Lanen Wei, Kunhan Xu, Ting Qi","doi":"10.1021/acs.orglett.4c04205","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04205","url":null,"abstract":"An isomerized bithiazole imide (iBTzI) acceptor was effectively synthesized and functionalized via Suzuki or Stille coupling reactions. Compared with the isomerized bithiophene imide (iBTI) and bithiazole imide (BTzI), iBTzI has a more planar skeleton. Furthermore, the conjugated skeleton of iBTzI can be extended by hydrogen and chalcogen bonds. The donor–acceptor–donor-type (D–A–D-type) iBTzI derivatives display blue-to-red emission and enhanced photoluminescence quantum yields (Φ<sub>PL</sub>s) in solution, showing great promise in luminous materials.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 6 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833015","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 Functionalization of the α,β-C–H Bonds in Alanine Ester Derivatives via Enamine–Imine Tautomerism: Construction of 4-Quinolinolate Skeletons through a Fragmentation–Reassembly Pathway 通过烯胺-烯胺同分异构实现丙氨酸酯衍生物中 α、β-C-H 键的双重官能化：通过碎片再组装途径构建 4-喹啉酸酯骨架
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04324
Jie Mao, Yue Hu, Shumiao He, Shuwei Zhang, Qiyuan Ma, Yu Yuan, Xiaodong Jia
{"title":"Dual Functionalization of the α,β-C–H Bonds in Alanine Ester Derivatives via Enamine–Imine Tautomerism: Construction of 4-Quinolinolate Skeletons through a Fragmentation–Reassembly Pathway","authors":"Jie Mao, Yue Hu, Shumiao He, Shuwei Zhang, Qiyuan Ma, Yu Yuan, Xiaodong Jia","doi":"10.1021/acs.orglett.4c04324","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04324","url":null,"abstract":"Using a SbCl<sub>3</sub>/O<sub>2</sub> mild oxidation system, a dual functionalization of the α,β-C–H bonds in alanine ester derivatives was achieved via enamine–imine tautomerism, and a series of quinoline-4-carboxylates were synthesized through a fragmentation–reassembly pathway. The investigation of the substrate scope revealed that various functional groups were easily tolerated, highlighting that this reaction provided an efficient path for the construction of the quinoline-4-carboxylate framework.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833019","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 Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines 通过 Cu(II)-Catalyzed Amination 和 N-氧化物与邻烷基苯胺之间的腈化反应合成喹啉-吲哚杂化物
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04375
Amitava Rakshit, Kyeongwon Moon, Pargat Singh, Jung Su Park, In Su Kim
{"title":"Synthesis of Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines","authors":"Amitava Rakshit, Kyeongwon Moon, Pargat Singh, Jung Su Park, In Su Kim","doi":"10.1021/acs.orglett.4c04375","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04375","url":null,"abstract":"The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline <i>N</i>-oxides with <i>o</i>-alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2′-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832780","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
Photocatalytic Hydrodichloromethylation of Unactivated Alkenes with Chloroform
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04367
Dawei Gong, Caiyu Gao, Yanlin Zhang, Fen Yao, Qixuan Li, Yufei Li, Lina Zhao, Degong Kong
{"title":"Photocatalytic Hydrodichloromethylation of Unactivated Alkenes with Chloroform","authors":"Dawei Gong, Caiyu Gao, Yanlin Zhang, Fen Yao, Qixuan Li, Yufei Li, Lina Zhao, Degong Kong","doi":"10.1021/acs.orglett.4c04367","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04367","url":null,"abstract":"A visible-light-induced method for the hydrodichloromethylation of unactivated alkenes using chloroform (CHCl<sub>3</sub>) was developed, employing pyridine·BH<sub>3</sub> as the halogen atom transfer (XAT) reagent. The strategy showed a broad functional group tolerance, and 29 examples of unactivated alkenes, including complex natural products or drug derivatives, have been established with good yields. Mechanistic studies indicated that CHCl<sub>3</sub> serves as both the source of a dichloromethyl radical and a hydrogen atom transfer (HAT) reagent, and the borane short-chain reaction process was involved in this system. This method represents a novel approach for hydrodichloromethylation of unactivated alkenes without using an additional HAT reagent.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"144 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833061","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
Boron-Doped Molecular Carbons Bearing a Formal Boron-Inserted Pentalene: Synthesis, Electronic Structures and Properties
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-16 DOI: 10.1021/acs.orglett.4c04168
Liuzhong Yuan, Jingyuan Yang, Peng Lv, Yujia Liu, Zeyi Li, Yue Wang, Chuandong Dou
{"title":"Boron-Doped Molecular Carbons Bearing a Formal Boron-Inserted Pentalene: Synthesis, Electronic Structures and Properties","authors":"Liuzhong Yuan, Jingyuan Yang, Peng Lv, Yujia Liu, Zeyi Li, Yue Wang, Chuandong Dou","doi":"10.1021/acs.orglett.4c04168","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04168","url":null,"abstract":"Two boron-doped molecular carbons (BMCs), featuring one formal boron-inserted pentalene (BP) embedded into the C<sub>20</sub>B or C<sub>28</sub>B polycyclic π-skeleton, were successfully synthesized. Despite their small-size conjugated structures, both of them exhibit unusual broad light absorption, narrow energy gaps, and electron-accepting ability, as well as local antiaromaticity with pseudo 4π electrons. As disclosed, these intriguing physical properties are significantly contributed by the boron atom and pentagonal ring in the BP substructure, thus demonstrating the importance of such BP incorporation into polycyclic π-systems.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833013","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
Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-13 DOI: 10.1021/acs.orglett.4c04069
Shimin Xie, Shuwang Tang, Ming Hou, Wenlin Xie, Meng Guan, Tianwen Bai, Linli He, Guanyinsheng Qiu
{"title":"Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes","authors":"Shimin Xie, Shuwang Tang, Ming Hou, Wenlin Xie, Meng Guan, Tianwen Bai, Linli He, Guanyinsheng Qiu","doi":"10.1021/acs.orglett.4c04069","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04069","url":null,"abstract":"In this work, the annulation of acyl nitrene with alkynes is reported under photoredox/iron dual-catalysis for the synthesis of a series of isoquninalin-2-ones. The reaction is featured with a high reaction regioselectivity and good reaction generality. In particular, the resulting isoquinalin-2-ones could be structurally elaborated into several biologically interesting scaffolds. Mechanism investigation suggests that the reaction was ascribed to a formal [4 + 2] cyclization. It is believed that this reaction represents an initial example of preparing isoquinolin-1-ones from ferric peroxyl-catalyzed nitrene insertion.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"42 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816366","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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