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HFIP-Promoted Regioselective Hydrofunctionalization of Enamides and N-Vinyl Azoles hfip促进酰胺类和n -乙烯基偶氮的区域选择性加氢功能化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-29 DOI: 10.1021/acs.joc.5c00378
Susanta Patra, Satyajit Samanta, Vishal Talukdar, Parthasarathi Das
{"title":"HFIP-Promoted Regioselective Hydrofunctionalization of Enamides and N-Vinyl Azoles","authors":"Susanta Patra, Satyajit Samanta, Vishal Talukdar, Parthasarathi Das","doi":"10.1021/acs.joc.5c00378","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00378","url":null,"abstract":"An efficient and regioselective method for the intermolecular hydrofunctionalization of enamides and <i>N</i>-vinyl azoles has been developed, enabling the formation of diverse C–S, C–O, C–N, and C–C bonds. This transition-metal-free, additive-free, and Brønsted acid-free protocol employs hexafluoroisopropanol (HFIP) as the sole reagent, which plays a dual role: formation of iminium carbocation intermediate and facilitating nucleophile generation through its hydrogen-bonding network. The reaction demonstrates exceptional substrate versatility, accommodating thiophenols, alcohols, heterocyclic amines, as well as <i>NH</i>-free indoles, pyrroles, and carbazoles as nucleophiles, proceeding via a Markovnikov-selective hydrofunctionalization pathway. The protocol is general and simple with broad substrate compatibility.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"81 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143885409","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
Formal Carbene Insertion into Cyclopropanones: Access to 2-Aroyl Cyclobutanones via Sulfonium Ylides 环丙烷的正式卡宾插入：通过磺酰化获得2-芳基环丁酮
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-29 DOI: 10.1021/acs.joc.5c00167
Ishika Agrawal, Marvin Lange, Arthur Semmelmaier, Heinrich F. von Köller, Daniel B. Werz
{"title":"Formal Carbene Insertion into Cyclopropanones: Access to 2-Aroyl Cyclobutanones via Sulfonium Ylides","authors":"Ishika Agrawal, Marvin Lange, Arthur Semmelmaier, Heinrich F. von Köller, Daniel B. Werz","doi":"10.1021/acs.joc.5c00167","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00167","url":null,"abstract":"This report presents a method for the synthesis of 2-aroyl cyclobutanones via the reaction of in situ-generated cyclopropanones with acyl sulfonium ylides representing a formal carbene insertion into cyclopropanones. The reaction is highly stereoselective in the case of 2-substituted cyclopropanones, and the cyclobutanones thus obtained are well suited to α-alkylation, offering versatile synthetic applications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143885408","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
One-Pot Synthesis of Benzoxazoles and Sulfoxides: Complete Utilization of Diaryl Sulfoxides 苯并恶唑和亚砜的一锅合成：二芳基亚砜的完全利用
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-29 DOI: 10.1021/acs.joc.5c0027410.1021/acs.joc.5c00274
Chuntao Zhong, Guangcai Qu, Jingdi Wang, Baoshan Xu, Benqiang Cui*, Yanhui Shi* and Changsheng Cao*, 
{"title":"One-Pot Synthesis of Benzoxazoles and Sulfoxides: Complete Utilization of Diaryl Sulfoxides","authors":"Chuntao Zhong,&nbsp;Guangcai Qu,&nbsp;Jingdi Wang,&nbsp;Baoshan Xu,&nbsp;Benqiang Cui*,&nbsp;Yanhui Shi* and Changsheng Cao*,&nbsp;","doi":"10.1021/acs.joc.5c0027410.1021/acs.joc.5c00274","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00274https://doi.org/10.1021/acs.joc.5c00274","url":null,"abstract":"<p >Synthesis of 2-aryl benzoxazoles and aryl sulfoxide derivatives in a one-pot process has been developed via the palladium-catalyzed cross-coupling of diaryl sulfoxides with benzoxazoles, followed by trapping the remaining sulfenate anions with different electrophilic reagents. The reaction involves the C–S and C–H bond activation and the C–C and C–S bond formation. The protocol allows a broad scope of substrates, functional group tolerance, and scalability.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 18","pages":"6208–6218 6208–6218"},"PeriodicalIF":3.3,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143921516","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
Pd-Catalyzed Regioselective Hydroxymethylation of Olefins with HCO2H via Sequential Hydroformylation and Reduction pd催化烯烃与HCO2H通过顺序氢甲酰化和还原的区域选择性羟甲基化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-29 DOI: 10.1021/acs.joc.5c00436
Wenlong Ren, Jinzi Huang, Jintao Ou, Xujian Sheng, Yuan Shi, Ke Huang, Yian Shi
{"title":"Pd-Catalyzed Regioselective Hydroxymethylation of Olefins with HCO2H via Sequential Hydroformylation and Reduction","authors":"Wenlong Ren, Jinzi Huang, Jintao Ou, Xujian Sheng, Yuan Shi, Ke Huang, Yian Shi","doi":"10.1021/acs.joc.5c00436","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00436","url":null,"abstract":"An effective Pd-catalyzed regioselective hydroxymethylation of olefins with HCO<sub>2</sub>H and Ac<sub>2</sub>O is described. A variety of primary alcohols can be obtained in up to 94% yield and a &gt;20:1 l:b ratio via sequential hydroformylation and reduction. The reaction is operationally simple with no need for external CO and H<sub>2</sub>.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890197","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
One-Pot Synthesis of Benzoxazoles and Sulfoxides: Complete Utilization of Diaryl Sulfoxides 苯并恶唑和亚砜的一锅合成：二芳基亚砜的完全利用
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-29 DOI: 10.1021/acs.joc.5c00274
Chuntao Zhong, Guangcai Qu, Jingdi Wang, Baoshan Xu, Benqiang Cui, Yanhui Shi, Changsheng Cao
{"title":"One-Pot Synthesis of Benzoxazoles and Sulfoxides: Complete Utilization of Diaryl Sulfoxides","authors":"Chuntao Zhong, Guangcai Qu, Jingdi Wang, Baoshan Xu, Benqiang Cui, Yanhui Shi, Changsheng Cao","doi":"10.1021/acs.joc.5c00274","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00274","url":null,"abstract":"Synthesis of 2-aryl benzoxazoles and aryl sulfoxide derivatives in a one-pot process has been developed via the palladium-catalyzed cross-coupling of diaryl sulfoxides with benzoxazoles, followed by trapping the remaining sulfenate anions with different electrophilic reagents. The reaction involves the C–S and C–H bond activation and the C–C and C–S bond formation. The protocol allows a broad scope of substrates, functional group tolerance, and scalability.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"44 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890278","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
HFIP-Promoted Regioselective Hydrofunctionalization of Enamides and N-Vinyl Azoles hfip促进酰胺类和n -乙烯基偶氮的区域选择性加氢功能化
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-29 DOI: 10.1021/acs.joc.5c0037810.1021/acs.joc.5c00378
Susanta Patra, Satyajit Samanta, Vishal Talukdar and Parthasarathi Das*, 
{"title":"HFIP-Promoted Regioselective Hydrofunctionalization of Enamides and N-Vinyl Azoles","authors":"Susanta Patra,&nbsp;Satyajit Samanta,&nbsp;Vishal Talukdar and Parthasarathi Das*,&nbsp;","doi":"10.1021/acs.joc.5c0037810.1021/acs.joc.5c00378","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00378https://doi.org/10.1021/acs.joc.5c00378","url":null,"abstract":"<p >An efficient and regioselective method for the intermolecular hydrofunctionalization of enamides and <i>N</i>-vinyl azoles has been developed, enabling the formation of diverse C–S, C–O, C–N, and C–C bonds. This transition-metal-free, additive-free, and Brønsted acid-free protocol employs hexafluoroisopropanol (HFIP) as the sole reagent, which plays a dual role: formation of iminium carbocation intermediate and facilitating nucleophile generation through its hydrogen-bonding network. The reaction demonstrates exceptional substrate versatility, accommodating thiophenols, alcohols, heterocyclic amines, as well as <i>NH</i>-free indoles, pyrroles, and carbazoles as nucleophiles, proceeding via a Markovnikov-selective hydrofunctionalization pathway. The protocol is general and simple with broad substrate compatibility.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 18","pages":"6261–6277 6261–6277"},"PeriodicalIF":3.3,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143921414","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
Formal Carbene Insertion into Cyclopropanones: Access to 2-Aroyl Cyclobutanones via Sulfonium Ylides 环丙烷的正式卡宾插入：通过磺酰化获得2-芳基环丁酮
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-29 DOI: 10.1021/acs.joc.5c0016710.1021/acs.joc.5c00167
Ishika Agrawal, Marvin Lange, Arthur Semmelmaier, Heinrich F. von Köller and Daniel B. Werz*, 
{"title":"Formal Carbene Insertion into Cyclopropanones: Access to 2-Aroyl Cyclobutanones via Sulfonium Ylides","authors":"Ishika Agrawal,&nbsp;Marvin Lange,&nbsp;Arthur Semmelmaier,&nbsp;Heinrich F. von Köller and Daniel B. Werz*,&nbsp;","doi":"10.1021/acs.joc.5c0016710.1021/acs.joc.5c00167","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00167https://doi.org/10.1021/acs.joc.5c00167","url":null,"abstract":"<p >This report presents a method for the synthesis of 2-aroyl cyclobutanones via the reaction of in situ-generated cyclopropanones with acyl sulfonium ylides representing a formal carbene insertion into cyclopropanones. The reaction is highly stereoselective in the case of 2-substituted cyclopropanones, and the cyclobutanones thus obtained are well suited to α-alkylation, offering versatile synthetic applications.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 18","pages":"6162–6168 6162–6168"},"PeriodicalIF":3.3,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.joc.5c00167","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143921430","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Iron-Catalyzed Regioselective C═C Bond Migration and Reductive Deuteration 铁催化的区域选择性C = C键迁移和还原氘化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-28 DOI: 10.1021/acs.joc.5c00449
Qiuting Zhao, Congrong Li, Hongjie Gao, Yu-Chen Cao, Rong-Zhen Liao, Wenguang Wang
{"title":"Iron-Catalyzed Regioselective C═C Bond Migration and Reductive Deuteration","authors":"Qiuting Zhao, Congrong Li, Hongjie Gao, Yu-Chen Cao, Rong-Zhen Liao, Wenguang Wang","doi":"10.1021/acs.joc.5c00449","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00449","url":null,"abstract":"We report a well-defined multifunctional iron catalyst, Cp*Fe(Ph<sub>2</sub>PN = C<sub>5</sub>H<sub>4</sub>N), that promotes the rearrangement of β,γ-unsaturated ketones, esters, and amides to their α,β-isomers, enabling regioselective C═C reductive deuteration. This iron-catalyzed protocol showcases the synthesis of a diverse range of α,β-dideuterated organic compounds, demonstrating broad substrate compatibility under mild conditions. Mechanism studies provide insights into the C═C bond relocation and cooperative D<sub>2</sub> activation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"73 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143885176","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
Tandem SNAr/Aldol Condensation of Oxindoles with o-Haloacetophenones Enables Modular Assembly of 2,3-Fused Indolines Bearing a Quaternary Carbon 氧吲哚与邻卤代苯乙酮的串联SNAr/Aldol缩合使含一个季碳的2,3-熔融吲哚的模块化组装成为可能
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-28 DOI: 10.1021/acs.joc.5c00301
Zi-Xia Zheng, Kai-Heng Yu, Zi-Yuan Liu, Qun Cai, Zi-Yi Yuan, Feng-Cheng Jia, Shuang-Xi Gu
{"title":"Tandem SNAr/Aldol Condensation of Oxindoles with o-Haloacetophenones Enables Modular Assembly of 2,3-Fused Indolines Bearing a Quaternary Carbon","authors":"Zi-Xia Zheng, Kai-Heng Yu, Zi-Yuan Liu, Qun Cai, Zi-Yi Yuan, Feng-Cheng Jia, Shuang-Xi Gu","doi":"10.1021/acs.joc.5c00301","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00301","url":null,"abstract":"Described herein is a novel base-promoted [4 + 2] annulation reaction of 3-methyl-indolin-2-ones with <i>ortho</i>-haloacetophenones, which enables the modular and reliable synthesis of 2,3-fused indolines bearing a quaternary carbon. Two C–C bonds can be successively constructed through a tandem sequence involving base-promoted S<sub>N</sub>Ar and aldol condensation. This protocol is highlighted by transition metal-free conditions, high efficiency, and simple operation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143880634","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
Oxa-Ferrier Rearrangement Reaction Mediated by TEMPO Cation and NaClO2: Application to the Total Synthesis of Passifetilactones B and C TEMPO阳离子和NaClO2介导的oxa -铁离子重排反应：在全合成钝化内酯B和C中的应用
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-04-28 DOI: 10.1021/acs.joc.5c0035410.1021/acs.joc.5c00354
Jocelyn Bautista-Nava, Luis F. Porras-Santos, Leticia Quintero, José Alvano Pérez-Bautista, Pedro López-Mendoza* and Fernando Sartillo-Piscil*, 
{"title":"Oxa-Ferrier Rearrangement Reaction Mediated by TEMPO Cation and NaClO2: Application to the Total Synthesis of Passifetilactones B and C","authors":"Jocelyn Bautista-Nava,&nbsp;Luis F. Porras-Santos,&nbsp;Leticia Quintero,&nbsp;José Alvano Pérez-Bautista,&nbsp;Pedro López-Mendoza* and Fernando Sartillo-Piscil*,&nbsp;","doi":"10.1021/acs.joc.5c0035410.1021/acs.joc.5c00354","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00354https://doi.org/10.1021/acs.joc.5c00354","url":null,"abstract":"<p >The TEMPO<sup>+</sup> (2,2,6,6-tetramethylpiperidine-<i>N</i>-oxyl cation) is a versatile chemical species commonly known as an oxidizing reagent. Nevertheless, its capability to act as a Lewis acid has been recently revealed. Here, we report a TEMPO<sup>+</sup>-promoted oxa-Ferrier rearrangement of glycals to chiral α,β-unsaturated δ-lactones using sodium chlorite (NaClO<sub>2</sub>) as a cheap and environmentally friendly oxidizing reagent. Since the vinylic oxocarbenium intermediate is trapped by chlorite ion to form a carbonyl group, we name this reaction as the “Oxa-Ferrier rearrangement”. Accordingly, this reaction is suitable for various <i>O</i>-acetylated, <i>O</i>-benzoylated, and <i>O</i>-benzylated glycals, providing the corresponding α,β-unsaturated δ-lactones in moderate to good yield. Additionally, the synthetic utility of this methodology was applied to the synthesis and confirmation of the absolute configuration of passifetilactones B and C.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 18","pages":"6251–6260 6251–6260"},"PeriodicalIF":3.3,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.joc.5c00354","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143921299","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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