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Cascade [3 + 2] Annulation of 1,3-Dicarbonyl Compounds and Ethyl Secondary Amines for Pyrrole Synthesis via Poly C(sp3)–H Bond Functionalization 通过多 C(sp3)-H-键官能团化实现 1,3-二羰基化合物与乙基仲胺的级联 [3 + 2] 嵌合以合成吡咯
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1021/acs.joc.4c02127
Xiuli Li, Yunyun Liu, Jie-Ping Wan
{"title":"Cascade [3 + 2] Annulation of 1,3-Dicarbonyl Compounds and Ethyl Secondary Amines for Pyrrole Synthesis via Poly C(sp3)–H Bond Functionalization","authors":"Xiuli Li, Yunyun Liu, Jie-Ping Wan","doi":"10.1021/acs.joc.4c02127","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02127","url":null,"abstract":"The synthesis of polyfunctionalized pyrroles via the cascade reactions of 1,3-dicarbonyl compounds and two molecules of ethyl secondary amines has been realized via simple iodine catalysis in the presence of Dess–Martin periodinane (DMP). The formation of the target pyrrole products involves the formation of one new C–C and two new C–N bonds via the major functionalization of six C(sp<sup>3</sup>)–H bonds, presenting a highly novel and efficient synthetic protocol toward pyrrole scaffolds.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452363","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Hydrogen Fluoride Imidazole: A Simple, Efficient, Mild, and Cost-Effective Silyl-Ether Deprotection Reagent 氟化氢咪唑：一种简单、高效、温和、经济的硅醚脱保护试剂
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1021/acs.joc.4c01885
Xuan Zhou, Yannick Fillon, Xianglin Shi, Firoz Antia, Xiao Zhou, Angela Lin
{"title":"Hydrogen Fluoride Imidazole: A Simple, Efficient, Mild, and Cost-Effective Silyl-Ether Deprotection Reagent","authors":"Xuan Zhou, Yannick Fillon, Xianglin Shi, Firoz Antia, Xiao Zhou, Angela Lin","doi":"10.1021/acs.joc.4c01885","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01885","url":null,"abstract":"Despite the availability of numerous −OH silyl protection and deprotection methods, the selective cleavage of silyl ethers in highly complex molecules can still be a challenge. In this article, we present results from a full investigation of a novel, efficient, and mild desilylation protocol using HF/imidazole. Imidazole significantly enhances the desilylation reaction efficiency of HF, allowing clean and complete deprotection of TBDPS ethers in substrates containing both acid and base sensitive groups. For example, four- and five-mer oligonucleotides were efficiently deprotected where all other conditions failed. HF/imidazole is also an effective reagent for the deprotection of TIPS and TBDMS ethers. The reagent prepared using commercially available HF and imidazole maintained the same reactivity even after 4 years of storage at 4 °C. Residual reagents and byproducts can be readily removed with a simple workup; consequently, deprotection of TBDPS was successfully implemented in a 2.5 kg scale synthesis of a five-mer oligonucleotide.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452361","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Catalytic Synthesis of 1H-Benzoxazolo[3,2-a]pyridin-1-ones via Formal [3 + 3] Annulations of NHC-Generated Alkynyl Acylazoliums with Benzoxazolyl Acetates and Their Photophysical Studies 通过 NHC 生成的炔吖啶鎓与苯并恶唑基乙酸酯的形式化 [3 + 3] 嵌合催化合成 1H 苯并恶唑并[3,2-a]吡啶-1-酮及其光物理研究
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1021/acs.joc.4c01616
Sibasis Sarkar, Suravi Das, Shikha Gandhi
{"title":"Catalytic Synthesis of 1H-Benzoxazolo[3,2-a]pyridin-1-ones via Formal [3 + 3] Annulations of NHC-Generated Alkynyl Acylazoliums with Benzoxazolyl Acetates and Their Photophysical Studies","authors":"Sibasis Sarkar, Suravi Das, Shikha Gandhi","doi":"10.1021/acs.joc.4c01616","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01616","url":null,"abstract":"We disclose the synthesis of a tricyclic fused N-heterocycle via the NHC-catalyzed annulation of either a ynal or an alkynyl ester with readily accessible benzoxazolyl acetate. While the annulation with ynals requires an oxidant, the reaction with alkynyl esters proceeds via the direct generation of alkynyl acylazolium intermediates with an NHC. With the dearth of catalytic processes to access these 1<i>H</i>-benzoxazolo[3,2-<i>a</i>]pyridin-1-ones from simple starting materials, this method is especially important. The photophysical properties of the products have also been evaluated.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452379","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Substrate-Induced Cooperative Ionic Catalysis: Difunctionalization of Indole Derivatives Employing Dimethyl Carbonate 底物诱导的离子合作催化：使用碳酸二甲酯的吲哚衍生物的双官能化
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1021/acs.joc.4c01619
Sangita Dattatray Shinde, Ashik Chhetri, Sayak Ghosh, Anusri Debnath, Pooja Joshi, Dinesh Kumar
{"title":"Substrate-Induced Cooperative Ionic Catalysis: Difunctionalization of Indole Derivatives Employing Dimethyl Carbonate","authors":"Sangita Dattatray Shinde, Ashik Chhetri, Sayak Ghosh, Anusri Debnath, Pooja Joshi, Dinesh Kumar","doi":"10.1021/acs.joc.4c01619","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01619","url":null,"abstract":"The global urge to adopt sustainable chemistry has resulted in the development of more environmentally benign strategies (EBS) that use CO<sub>2</sub> and CO<sub>2</sub>-derived chemicals in a step-economic manner. In this context, we investigated a dual C–H methylation and (C═O)-methoxylation of indole derivatives using dimethyl carbonate (DMC) in the presence of catalytic amounts of Cs<sub>2</sub>CO<sub>3</sub>. Mechanistic insights include DMF-assisted, DMC-induced cooperative ionic catalysis, which allows DMC to act as both a nucleophilic and an electrophilic precursor, resulting in (C═O)-methoxylation and C–H methylation of <i>N</i>-benzylindolyl ketones.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Skeletal Reorganization Emanated via the Course of Heterocyclic N1–N2 Bond Cleavage: Electrosynthetic Approach 杂环 N1-N2 键裂解过程中产生的骨架重组：电合成方法
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-20 DOI: 10.1021/acs.joc.4c01820
Saiful Islam, Dwaipayan Das, Rahul Dev Mandal, Samiran Dhara, Asish R Das
{"title":"Skeletal Reorganization Emanated via the Course of Heterocyclic N1–N2 Bond Cleavage: Electrosynthetic Approach","authors":"Saiful Islam, Dwaipayan Das, Rahul Dev Mandal, Samiran Dhara, Asish R Das","doi":"10.1021/acs.joc.4c01820","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01820","url":null,"abstract":"A unified method toward the synthesis of functionalized diazepines and quinazolines through reorganization of the molecular skeleton has been devised. The process is indulged by electrical energy via a domino N<sup>1</sup>–N<sup>2</sup> bond cleavage followed by concomitant ring closing, initiating from cinnolines and indazoles as designed precursors. Additionally, an intermolecular ring homologation has also been established to synthesize densely functionalized dihydroquinazolines from 2,3-diaryl-indazoles and acetonitrile involving the same electrochemical strategy.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142451709","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 α-Carbonyl-α′-sulfenyl Sulfoxonium Ylides in Water at Room Temperature 室温下在水中合成 α-羰基-α′-亚磺酰亚磺酰胺
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-19 DOI: 10.1021/acs.joc.4c01592
Haoyu Tian, Qinghe Wang, Wenyan Wei, Yan Chen, Xia Zhong, Guiwei Yao, Xun Chen, Guangkuan Zhao, Dulin Kong
{"title":"Synthesis of α-Carbonyl-α′-sulfenyl Sulfoxonium Ylides in Water at Room Temperature","authors":"Haoyu Tian, Qinghe Wang, Wenyan Wei, Yan Chen, Xia Zhong, Guiwei Yao, Xun Chen, Guangkuan Zhao, Dulin Kong","doi":"10.1021/acs.joc.4c01592","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01592","url":null,"abstract":"An efficient synthesis of α-carbonyl-α′-sulfenyl sulfoxonium ylides through a KIO<sub>3</sub>-promoted cross-dehydrogenative coupling reaction of aryl thiols and α-carbonyl sulfoxonium ylides in an aqueous medium at room temperature has been described. The α-carbonyl sulfoxonium ylides and aryl thiols adorned with various functional groups were well-tolerated and afforded moderate to high yields of α-carbonyl-α<i>′</i>-sulfenyl sulfoxonium ylide derivatives. Finally, by converting synthesized ylide <b>3a</b> into other valuable compounds, we demonstrated the practicality of this synthetic method.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142449838","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Moderation of the Electronic Structure of Phosphamides to Execute the Catalytic Appel Reaction Bypassing Phosphine 调节膦酰胺的电子结构以绕过膦进行催化阿贝尔反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-19 DOI: 10.1021/acs.joc.4c02006
Nidhi Kumari, Anjana Jagadeesh, Prashant Galav, Avinava Kundu, Biswarup Chakraborty
{"title":"Moderation of the Electronic Structure of Phosphamides to Execute the Catalytic Appel Reaction Bypassing Phosphine","authors":"Nidhi Kumari, Anjana Jagadeesh, Prashant Galav, Avinava Kundu, Biswarup Chakraborty","doi":"10.1021/acs.joc.4c02006","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02006","url":null,"abstract":"A set of structurally analogous, albeit electronically distinct, phosphamides (<b>1aa-10aa</b>) is prepared, and the effect of the electronic amendment due to p-substitution has been tested for the conversion of alcohols to halides via the Appel reaction. The −OMe-substituted diphosphamide (<b>8aa</b>) remains the most active, providing ∼96% conversion of alcohols to halides with a TON of 11 in moderate reaction conditions with a large substrate scope. Halide formation follows a pseudo-first-order rate with a constant rate (<i>k</i><sub>obs</sub>) of 7.13 × 10<sup>–5</sup> s<sup>–1</sup>. Temp-dependent kinetics and Eyring analyses reveal the activation parameters Δ<i>H</i><sup>‡</sup> of 28.95 (±1.6) kcal mol<sup>–1</sup>, Δ<i>S</i><sup>‡</sup> of −70.02 (±0.4) cal K<sup>–1</sup> mol<sup>–1</sup>, and Δ<i>G</i><sup>‡</sup><sub>298</sub> of 49.81 (±1.2) kcal mol<sup>–1</sup>. The deuterium labeling study highlights the O–H dissociation of the alcohol as the rate-determining step, while the Hammett analysis with <i>p</i>-substituted benzyl alcohols indicates a positive charge accumulation at the phosphorus center during the Appel reaction. The HOMO–LUMO energy and NPA analyses show that <i>p</i>–OMe substitutions in <b>8aa</b> make the “P═O” bond more ionic and corresponding aminophosphine is nucleophilic, which are favorable for the Appel reaction. In situ detection of the Appel salt, [R<sub>3</sub>PX]CX<sub>3</sub> and alkoxy phosphonium cation [R<sub>3</sub>POR]X, validates the reaction pathway mediated by the phosphamides.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142449840","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Development of a Divergent Synthesis Strategy for 5-Sulfonyl-Substituted Uracil Derivatives 开发 5-磺酰基取代的尿嘧啶衍生物的不同合成策略
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-18 DOI: 10.1021/acs.joc.4c01357
Lukas von Bredow, Alexander Fürll, Maik Tretbar
{"title":"Development of a Divergent Synthesis Strategy for 5-Sulfonyl-Substituted Uracil Derivatives","authors":"Lukas von Bredow, Alexander Fürll, Maik Tretbar","doi":"10.1021/acs.joc.4c01357","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01357","url":null,"abstract":"An efficient, diversity-orientated synthesis of 5-sulfone-substituted uracils was established. The use of protecting groups to synthesize sulfones from <i>N</i>-heterocycles was avoided. Various heterocycles were synthesized for the first time from favorable, easily accessible starting materials. Diversity-orientated syntheses are important for the medicinal chemistry of virostatics and chemotherapeutics. This approach provides a broad substrate tolerance and excellent yields of up to 98%.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142448204","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
TCCA/RSeSeR-Mediated Selenoalkoxy of Allenamides via a Radical Process: Synthesis of Selanyl-allylic N,O-Aminals TCCA/RSeSeR 通过自由基过程介导的烯酰胺硒烷氧基化：硒基烯丙基 N,O-氨基的合成
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-18 DOI: 10.1021/acs.joc.4c01601
Qingsong Liu, Jiri Gele, Kun Zhao, Shuting Zhang, Wen Gu, Zhigang Zhao, Xiaoxiao Li
{"title":"TCCA/RSeSeR-Mediated Selenoalkoxy of Allenamides via a Radical Process: Synthesis of Selanyl-allylic N,O-Aminals","authors":"Qingsong Liu, Jiri Gele, Kun Zhao, Shuting Zhang, Wen Gu, Zhigang Zhao, Xiaoxiao Li","doi":"10.1021/acs.joc.4c01601","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01601","url":null,"abstract":"An efficient TCCA (trichloroisocyanuric acid)/RSeSeR-mediated selenoalkoxy of allenamides for the construction of selanyl-allylic N,OA-aminal derivatives was developed. The reaction exhibits good functional group tolerance and high efficiency, affording the products in good to excellent yields. Mechanistic investigations indicated that a selanyl-allylic radical intermediate was first formed via the RSe radical added to the central carbon of allenamides, which subsequently furnished highly stable selanyl-allylic carbocation intermediate by abstraction of an electron by the chlorine radical. Moreover, this is the first report of using selenium reagent (RSeCl) to activate allenamides via a radical process.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142448341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Ring Opening Reduction of Cyclic Anhydrides Catalyzed by Tris(pentafluorophenyl)borane Using Hydrosilanes as a Hydride Source 利用氢硅烷作为氢化物源，在三(五氟苯基)硼烷催化下实现环酐的开环还原
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-10-18 DOI: 10.1021/acs.joc.4c01179
Vladimir V. Zotov, Carl Zupancic, Zachary J. Bailey, Guodong Du
{"title":"Ring Opening Reduction of Cyclic Anhydrides Catalyzed by Tris(pentafluorophenyl)borane Using Hydrosilanes as a Hydride Source","authors":"Vladimir V. Zotov, Carl Zupancic, Zachary J. Bailey, Guodong Du","doi":"10.1021/acs.joc.4c01179","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01179","url":null,"abstract":"Hydrosilanes are widely used as reducing agents in the reduction of carbonyl groups, and various catalysts have been developed for the activation of hydrosilanes, the majority of them being transition metal-based. A main-group-based Lewis acid tris(pentafluorophenyl)borane (BCF) has gained increasing attention due to its Lewis acidity and versatility, along with being nonmetal. Herein, we describe the BCF-catalyzed ring opening reduction of cyclic anhydrides using hydrosilanes as a source of hydrides. The reduction affords unsymmetrical bis(silyl) protected hydroxy acids, leading to an efficient way for the synthesis of silyl ester functionalities. The capability of forming protected hydroxy acids under mild conditions with high yields in one step is also advantageous. A range of hydrosilanes and cyclic anhydrides can be employed with quantitative conversion, high yields, relatively fast reaction time, and mild reaction conditions. NMR spectroscopy is used in the characterization of the products, along with gaining insight into the potential mechanism.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142448338","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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