发布求助
文献互助 智能选刊 最新文献

Organic chemistry frontiers : an international journal of organic chemistry最新文献

筛选
英文 中文
Visible-light-mediated cobaloxime-catalyzed isomerization and hydroalkenylation of bicyclo[1.1.0]butanes† 可见光介导的钴肟催化双环[1.1.0]丁烷异构化和氢烯化反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d5qo00020c
Ben Mao , Sheng-Hao Jiang , Zheng Xiong , Yin Wei , Min Shi
{"title":"Visible-light-mediated cobaloxime-catalyzed isomerization and hydroalkenylation of bicyclo[1.1.0]butanes†","authors":"Ben Mao ,&nbsp;Sheng-Hao Jiang ,&nbsp;Zheng Xiong ,&nbsp;Yin Wei ,&nbsp;Min Shi","doi":"10.1039/d5qo00020c","DOIUrl":"10.1039/d5qo00020c","url":null,"abstract":"<div><div>Bicyclo[1.1.0]butanes have received extensive attention from chemists in recent years and diverse approaches to access transformations of such strained molecules have been explored. Although cobalt catalysis has become a promising field in organic synthesis, the cobalt-catalyzed strain-release strategy of bicyclobutanes is still underdeveloped. Herein, we disclose a visible-light-driven cobaloxime-catalyzed protocol for bicyclo[1.1.0]butane transformations. A range of cyclobutene and alkenylated cyclobutane products have been obtained in moderate to excellent yields with excellent functional group tolerance. Synthetic applications of this protocol were conducted with several transformations. Moreover, a series of control experiments and spectroscopic experiments were performed to demonstrate the reaction mechanism.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1958-1965"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142990905","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoredox-catalyzed selective head-to-head reductive coupling of activated alkenes†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02344g
Shenhao Chen , Zongchang Han , Han-Shi Hu , Jun Li , Chanjuan Xi
{"title":"Photoredox-catalyzed selective head-to-head reductive coupling of activated alkenes†","authors":"Shenhao Chen ,&nbsp;Zongchang Han ,&nbsp;Han-Shi Hu ,&nbsp;Jun Li ,&nbsp;Chanjuan Xi","doi":"10.1039/d4qo02344g","DOIUrl":"10.1039/d4qo02344g","url":null,"abstract":"<div><div>Head-to-head reductive hydrodimerization of activated alkenes offers access to valuable bulk or fine chemicals such as adipates or adiponitrile as an intermediate for the industrial synthesis of nylon. We herein report a novel reaction to realize head-to-head reductive coupling of activated alkenes by a photoinduced Ir/PPh<sub>3</sub>/H<sub>2</sub>O system, providing smooth access to various adipate derivatives in high chemo- and regioselectivity. In this reaction, a [Ph<sub>3</sub>P-OH] radical generated from a photoinduced interaction between H<sub>2</sub>O and PPh<sub>3</sub> enables the PCET process with activated alkenes to form a C-centered radical at the β-position, which is rarely reported.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 2011-2017"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d4qo02344g?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030895","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Diverse C(sp3)–H functionalizations through electrochemical benzylic oxygenation† 不同的C(sp3) -H通过电化学苯氧化功能化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02022g
Yan He , Tian-Sheng Chen , Xuesen Fan , Hai-Chao Xu
{"title":"Diverse C(sp3)–H functionalizations through electrochemical benzylic oxygenation†","authors":"Yan He ,&nbsp;Tian-Sheng Chen ,&nbsp;Xuesen Fan ,&nbsp;Hai-Chao Xu","doi":"10.1039/d4qo02022g","DOIUrl":"10.1039/d4qo02022g","url":null,"abstract":"<div><div>Despite significant advances in C(sp<sup>3</sup>)–H bond functionalization, the development of methods that are site-selective and capable of diverse bond formation remains a challenge. In addition, the preparation of olefins from aliphatics through cleavage of vicinal C(sp<sup>3</sup>)–H bonds remains difficult due to a lack of stereoselectivity and over-oxidation. To address these challenges, we have developed a transition metal catalyst- and external oxidant-free electrochemical C(sp<sup>3</sup>)–H oxygenation platform that enables highly stereoselective synthesis of aryl alkenes and diverse benzylic functionalizations to form various C–C and C–heteroatom bonds. This method involves site-selective benzylic C(sp<sup>3</sup>)–H trifluoroacetoxylation followed by elimination or substitution with diverse carbon- or heteroatom-based nucleophiles to form functionalized products. The utility of this protocol is further demonstrated by the desaturation of methyl dehydroabietate at the decagram scale and transformations of the resulting alkene. This study provides a platform for the diversity-oriented functionalization of both simple alkyl arenes and complex molecules.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1850-1857"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142986061","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Access to (bridged) bicyclic ureas through azocarboxamide-enabled enantioselective 1,2-diamination of α-branched cyclic ketones† 偶氮羧酰胺使α-支化环酮对映选择性1,2-二化获得（桥）双环脲
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02318h
Li Li , Yuan-Yang Li , Bei-Bei Li , Linlin Shi , Beiling Gao , Guang-Jian Mei
{"title":"Access to (bridged) bicyclic ureas through azocarboxamide-enabled enantioselective 1,2-diamination of α-branched cyclic ketones†","authors":"Li Li ,&nbsp;Yuan-Yang Li ,&nbsp;Bei-Bei Li ,&nbsp;Linlin Shi ,&nbsp;Beiling Gao ,&nbsp;Guang-Jian Mei","doi":"10.1039/d4qo02318h","DOIUrl":"10.1039/d4qo02318h","url":null,"abstract":"<div><div>Chiral bicyclic ureas are important multi-nitrogen-containing polycyclic frameworks and valuable building blocks in organic synthesis. Although many racemic synthetic methods have been reported, their catalytic asymmetric synthesis remains challenging and elusive. Herein, we report the azocarboxamide-enabled enantioselective 1,2-diamination of α-branched cyclic ketones. Under mild conditions, a wide range of fused bicyclic ureas bearing vicinal N-containing quaternary stereocenters have been prepared in good yield with excellent enantioselectivity. Notably, when α-carbethoxy cyclic ketones are used as substrates, the reaction proceeds through a cascade of 1,2-diaminization/lactonization, which leads to the formation of highly crowded and structurally unique bridged bicyclic ureas.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1772-1777"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142937394","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Indazole enhances Ru-catalyzed hydrogenation of unsaturated bonds†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02176b
Wenjun Jiang , Xiulin Li , Yaru Liu , Chunyan Zhang , Guoying Zhang , Ali Morsali
{"title":"Indazole enhances Ru-catalyzed hydrogenation of unsaturated bonds†","authors":"Wenjun Jiang ,&nbsp;Xiulin Li ,&nbsp;Yaru Liu ,&nbsp;Chunyan Zhang ,&nbsp;Guoying Zhang ,&nbsp;Ali Morsali","doi":"10.1039/d4qo02176b","DOIUrl":"10.1039/d4qo02176b","url":null,"abstract":"<div><div>The catalytic hydrogenation process is highly coveted and holds high potential due to its efficient conversion of crucial molecules into environmentally friendly alcohols, showcasing exceptional atom efficiency and selectivity. Moreover, these alcohol products serve as versatile precursors for synthesizing various pharmaceuticals. Herein, we have developed a practical and efficient procedure for the hydrogenation of various unsaturated compounds using Ru-catalysis with an indazole backbone PNN pincer ligand. This method effectively tackles the challenge of chemoselectivity in multifunctional hydrogenation reactions involving CC/N/O and CC bonds. The Ru catalytic system exhibits exceptional performance in the scalable synthesis of PNN ligands, achieving a turnover number of 63 371 and producing 146.18 grams of alcohol with a catalyst concentration as low as 0.001 mol%.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1936-1944"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143044758","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cooperative iridium and organocatalysis: a new frontier in asymmetric chemistry 合作铱与有机催化：不对称化学的新领域
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02430c
Divakar Chaudhary , Rakesh K. Saunthwal
{"title":"Cooperative iridium and organocatalysis: a new frontier in asymmetric chemistry","authors":"Divakar Chaudhary ,&nbsp;Rakesh K. Saunthwal","doi":"10.1039/d4qo02430c","DOIUrl":"10.1039/d4qo02430c","url":null,"abstract":"<div><div>The cooperative catalyst approach has become a significant and burgeoning area in synthetic organic chemistry, garnering substantial attention from the scientific community in recent years. Unlike single metal catalysts or organocatalysts, the cooperative catalysis strategy enables previously unattainable transformations to be accomplished in a stereocontrolled manner with high efficiency. In particular, cooperative iridium–organocatalysis has emerged as a valuable tool for producing biologically active chiral molecules from easily accessible starting materials. Iridium metal catalysts have been effectively combined with a diverse range of organocatalysts, including Brønsted acids, Lewis bases, N-heterocyclic carbene catalysts, and even phase transfer catalysts. This review provides a comprehensive overview of this evolving field, encompassing reaction advancements and mechanistic insights, to offer readers a better understanding of how metal–organic catalysts influence reaction mechanisms and the suitable starting materials for each catalytic process.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 2025-2051"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143050735","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Progress in the catalytic enantioselective construction of difluoroalkylated stereogenic centers 二氟烷基化立体中心催化对映选择性构建的研究进展
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02309a
Li-Juan Tang , Yongshun Wen , Hong-Xian Jin , Wenjun Luo , Lipeng Long , Jiayi Shen , Haiqing Luo , Daohong Yu
{"title":"Progress in the catalytic enantioselective construction of difluoroalkylated stereogenic centers","authors":"Li-Juan Tang ,&nbsp;Yongshun Wen ,&nbsp;Hong-Xian Jin ,&nbsp;Wenjun Luo ,&nbsp;Lipeng Long ,&nbsp;Jiayi Shen ,&nbsp;Haiqing Luo ,&nbsp;Daohong Yu","doi":"10.1039/d4qo02309a","DOIUrl":"10.1039/d4qo02309a","url":null,"abstract":"<div><div>Molecules bearing difluoroalkyl groups are very important in pharmaceuticals, agrochemicals, and many materials. In recent years, significant attention has been paid to the development of novel synthetic methods for constructing compounds containing CF<sub>2</sub>R groups. In particular, the construction of difluoroalkylated stereogenic centers is thriving. This review focuses on catalytic asymmetric difluoroalkylation for the construction of difluoralkylated stereogenic centers, summarizing the reported synthetic methods, the active intermediates involved, and the asymmetric strategies applied. The product diversity, selectivity, and proposed mechanisms are highlighted, and the future outlook and existing challenges are also provided.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 2052-2075"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142961290","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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-driven anion relay chemistry (ARC): construction of fully substituted pyrazoles† 可见光驱动的阴离子中继化学（ARC）：全取代吡唑的构建
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02072c
Guodan Lu , Tao Zhang , Xionglve Cheng , Kehan Qian , Yong Wang , Xiaobing Wan
{"title":"Visible-light-driven anion relay chemistry (ARC): construction of fully substituted pyrazoles†","authors":"Guodan Lu ,&nbsp;Tao Zhang ,&nbsp;Xionglve Cheng ,&nbsp;Kehan Qian ,&nbsp;Yong Wang ,&nbsp;Xiaobing Wan","doi":"10.1039/d4qo02072c","DOIUrl":"10.1039/d4qo02072c","url":null,"abstract":"<div><div>Anion relay chemistry (ARC) is a multi-component union strategy that has emerged as a powerful approach for synthesizing complex structures. However, previous studies have primarily concentrated on thermally controlled reaction modes. In this study, we report the development of an unprecedented visible-light-driven anion relay chemistry (ARC) strategy. Utilizing an energy-transfer process, we successfully transformed tosylhydrazones into anionic donors, facilitating the synthesis of fully substituted pyrazole derivatives under mild conditions. Furthermore, a combination of experimental mechanistic investigations and computational studies (DFT) not only corroborated the proposed mechanism of the reaction but also inspired additional avenues for future research.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1885-1892"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975425","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Access to chiral 3-benzylchromanones and 2,6-disubstituted cyclohexanones via Rh-catalyzed chemo- and enantioselective hydrogenation of arylidene chromanones/cyclohexanones†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02376e
Qianling Guo , Chaochao Xie , Guofu Zi , Yuping Huang , Guohua Hou
{"title":"Access to chiral 3-benzylchromanones and 2,6-disubstituted cyclohexanones via Rh-catalyzed chemo- and enantioselective hydrogenation of arylidene chromanones/cyclohexanones†","authors":"Qianling Guo ,&nbsp;Chaochao Xie ,&nbsp;Guofu Zi ,&nbsp;Yuping Huang ,&nbsp;Guohua Hou","doi":"10.1039/d4qo02376e","DOIUrl":"10.1039/d4qo02376e","url":null,"abstract":"<div><div>A highly chemo- and enantioselective hydrogenation of arylidene chromanones/cyclohexanones catalyzed by the Rh-f-spiroPhos complex has been developed, providing a series of chiral 3-benzylchromanones in high yields (93–99%) with excellent enantioselectivities (up to 98% ee) and achieving high turnover numbers (TON = 2000). Furthermore, an efficient desymmetrizing enantioselective hydrogenation of 3,5-dibenzylidene chromanones and 2,6-dibenzylidene cyclohexanones has also been realized, delivering chiral dibenzyl chromanones/cyclohexanones with excellent chemo-, diastereo- and enantioselectivities (up to &gt;20 : 1 <em>trans</em> : <em>cis</em>, &gt;99% ee). This methodology provides straightforward and mild access to the asymmetric synthesis of α-chiral ketones.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 2004-2010"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Highly selective visible-light-induced cascade cyclization of vinyl sulfoxonium ylides with azides: a novel synthetic approach towards trisubstituted furans† 高选择性可见光诱导叠氮基亚砜酰乙烯级联环化：合成三取代呋喃的新方法
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI: 10.1039/d4qo02195a
Jia-Huan Cui , Mei Tan , Jun Zhang , Yan He , Xingguang Li , Pei-Nian Liu
{"title":"Highly selective visible-light-induced cascade cyclization of vinyl sulfoxonium ylides with azides: a novel synthetic approach towards trisubstituted furans†","authors":"Jia-Huan Cui ,&nbsp;Mei Tan ,&nbsp;Jun Zhang ,&nbsp;Yan He ,&nbsp;Xingguang Li ,&nbsp;Pei-Nian Liu","doi":"10.1039/d4qo02195a","DOIUrl":"10.1039/d4qo02195a","url":null,"abstract":"<div><div>A simple protocol for the synthesis of trisubstituted furans <em>via</em> visible-light-driven regioselective cascade cyclization of vinyl sulfoxonium ylides with azides has been achieved. The reaction proceeds through the formation of a novel α-enone-α′-amide sulfoxonium ylide, which undergoes cyclization upon blue light irradiation to yield a trisubstituted furan scaffold. This method offers advantages including the absence of transition metals and photocatalysts, and the desired trisubstituted furans were prepared in good to excellent yields.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1905-1910"},"PeriodicalIF":0.0,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142975558","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
首页 上一页 下一页 尾页
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们：info@booksci.cn Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号：481959085
Book学术官方微信