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
An efficient direct phosphinylation and alkylation of ketones to construct C–P and C–C bonds: access to α,α-disubstituted γ-ketophosphine oxides† 酮的有效直接膦化和烷基化以构建C–P和C–C键：获得α，α-二取代的γ-酮膦氧化物†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01749k
Xiao-Hong Wei , Xiao-Hong Wang , Chun-Yuan Bai , Ya-Wen Xue , Ping Zhang , Yan-Bin Wang , Qiong Su
{"title":"An efficient direct phosphinylation and alkylation of ketones to construct C–P and C–C bonds: access to α,α-disubstituted γ-ketophosphine oxides†","authors":"Xiao-Hong Wei ,&nbsp;Xiao-Hong Wang ,&nbsp;Chun-Yuan Bai ,&nbsp;Ya-Wen Xue ,&nbsp;Ping Zhang ,&nbsp;Yan-Bin Wang ,&nbsp;Qiong Su","doi":"10.1039/d2qo01749k","DOIUrl":"10.1039/d2qo01749k","url":null,"abstract":"<div><p>The first example of an acid-promoted difunctionalization of ketones to construct C–P and C–C bonds <em>via</em> a phospha-aldol-elimination is described under metal- and solvent-free conditions. The cascade α-phosphorylation and α-alkylation sequence directly converts ketones to α,α-disubstituted γ-ketone phosphine oxides, thereby providing a new strategy for the synthesis of the α,α-disubstituted γ-ketone phosphine oxide anticholinesterase skeleton in moderate to excellent yields with water as the only by-product. Detailed mechanistic experiments verified that the reaction proceeds <em>via</em> a TfOH-induced carbocationic intermediate formed after the α-phosphorylation of ketones.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 2","pages":"Pages 410-415"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694207","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
Anion effect on enantioselective oxidative NHC catalysis: highly efficient kinetic resolution of tertiary alcohols and beyond† 阴离子对对映选择性氧化NHC催化的影响：叔醇及以上的高效动力学拆分†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01506d
Dan Hu , Si Bei Poh , Feipeng Liu , Zhifeng Tu , Xia Wang , Shenci Lu , Yu Zhao
{"title":"Anion effect on enantioselective oxidative NHC catalysis: highly efficient kinetic resolution of tertiary alcohols and beyond†","authors":"Dan Hu ,&nbsp;Si Bei Poh ,&nbsp;Feipeng Liu ,&nbsp;Zhifeng Tu ,&nbsp;Xia Wang ,&nbsp;Shenci Lu ,&nbsp;Yu Zhao","doi":"10.1039/d2qo01506d","DOIUrl":"10.1039/d2qo01506d","url":null,"abstract":"The effect of the counter-anion in the azolium pre-catalyst on enantio-control in oxidative NHC catalysis is demonstrated systematically for the first time in acylative kinetic resolution of oxindole-derived tertiary alcohols.","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 2","pages":"Pages 416-421"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694215","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
Photocatalytic dehydrations for the Ritter reaction† Ritter反应的光催化脱水†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo02046g
Lei Bao , Bei-Bei Zhang , Zhi-Xiang Wang , Xiang-Yu Chen
{"title":"Photocatalytic dehydrations for the Ritter reaction†","authors":"Lei Bao ,&nbsp;Bei-Bei Zhang ,&nbsp;Zhi-Xiang Wang ,&nbsp;Xiang-Yu Chen","doi":"10.1039/d2qo02046g","DOIUrl":"10.1039/d2qo02046g","url":null,"abstract":"<div><p>The Ritter reaction is a powerful method for the synthesis of amides; however, the photoinduced Ritter reaction of alcohols is rarely reported. We herein report a simple and additive-free photocatalytic dehydration method for the efficient direct conversion of benzyl alcohols to the corresponding amides using an organic photocatalyst 2,4,6-triphenylpyrylium salt. Experimental and computational mechanistic analyses show that a non-conventional generation process of a carbocation is involved in this photoinduced Ritter reaction.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 6","pages":"Pages 1375-1379"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3829679","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: 1
Electrophotocatalytic tri- or difluoromethylative cyclization of alkenes† 烯烃的电光催化三氟甲基化或二氟甲基化环化†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00290j
Danna Chen , Xuege Yang , Dongyin Wang , Yanni Li , Lou Shi , Deqiang Liang
{"title":"Electrophotocatalytic tri- or difluoromethylative cyclization of alkenes†","authors":"Danna Chen ,&nbsp;Xuege Yang ,&nbsp;Dongyin Wang ,&nbsp;Yanni Li ,&nbsp;Lou Shi ,&nbsp;Deqiang Liang","doi":"10.1039/d3qo00290j","DOIUrl":"10.1039/d3qo00290j","url":null,"abstract":"<div><p>We describe an electrophotocatalytic tri- or difluoromethylation/cyclization cascade of alkenes with fluoromethanesulfinate salts. This external-oxidant-free oxidative cyclization proceeds under mild electrode potentials yet is robust, and it is applicable to a broad range of alkenes, either activated or unactivated, affording a diverse array of fluoromethylated heterocycles with good functional-group tolerance using the inexpensive photocatalyst eosin Y. Of note is that an unactivated olefin is generally not accommodated by previous oxidative cyclization of alkenes unless a strong chemical oxidant is present. The protocol is amenable to the late-stage diversification of complex molecular architectures as well as a gram-scale synthesis, and sunlight could serve as the light source. Preliminary mechanistic studies suggest the merger of electrolysis with the reductive quenching photocatalytic cycle of eosin Y.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 10","pages":"Pages 2482-2490"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830480","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: 1
Fe/S cluster catalyzed cascade cyclization of N,S-1,6-enynes for the synthesis of thieno[3,4-b]indoles† Fe/S簇合物催化N，S-1,6-炔烃级联环化合成噻吩并[3,4-b]吲哚†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00697b
Zhuqing Liu , Shaobin Sun , Jiang Lou
{"title":"Fe/S cluster catalyzed cascade cyclization of N,S-1,6-enynes for the synthesis of thieno[3,4-b]indoles†","authors":"Zhuqing Liu ,&nbsp;Shaobin Sun ,&nbsp;Jiang Lou","doi":"10.1039/d3qo00697b","DOIUrl":"10.1039/d3qo00697b","url":null,"abstract":"<div><p>Fe/S cluster catalyzed radical cascade cyclization of alkylthio-functionalized <em>o</em>-anilide-embedded <em>N</em>,<em>S</em>-1,6-enynes to afford thieno[3,4-<em>b</em>]indoles is developed. The cycloisomerization strategy offers a straightforward route to 4<em>H</em>-thieno[3,4-<em>b</em>]indoles through the 1,2-sulfur transfer and Csp<sup>3</sup>–S bond cleavage, with the formation of both an indole ring and a fused thiophene ring in one pot. In this cascade, the element sulfur acts as the oxidant to induce the single electron transfer (SET) process.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 14","pages":"Pages 3637-3641"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830492","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
Pyrene bridged double[7]helicene embedded with a heptagonal ring† 芘桥接双[7]螺旋烯嵌入七边形环†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00386h
Asim Swain , Prince Ravat
{"title":"Pyrene bridged double[7]helicene embedded with a heptagonal ring†","authors":"Asim Swain ,&nbsp;Prince Ravat","doi":"10.1039/d3qo00386h","DOIUrl":"10.1039/d3qo00386h","url":null,"abstract":"<div><p>To utilize [<em>n</em>]helicene-embedded polycyclic aromatic hydrocarbons in the development of circularly polarized materials high luminescence quantum yield and dissymmetric factors are essential to boost (chir)optical properties. Previously we have shown that the (chir)optical properties of pyrene fused mono helicenes can be significantly influenced by the fusing mode and molecular symmetry. We report in this manuscript the stereospecific synthesis and (chir)optical properties of <em>C</em><sub>1</sub> symmetric pyrene fused double [7]helicene, where the helicene units are connected <em>via</em> hexagonal and heptagonal rings. In line with single helicene congeners, lower symmetric heptagon containing double helicene exhibited higher absorption and emission dissymmetric factors along with a significant increase in fluorescence quantum yield. Our findings in this manuscript provide further insights into the effect of molecular symmetry on the (chir)optical properties of single and double helicenes.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3714-3725"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830500","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
Shape-shifting p-cyclophanes as portals to switching, sensing, delivery and logic operations in water† 形状变换p-环面作为门户开关，传感，交付和逻辑操作在水中†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo02043b
Chao-Yi Yao , Hong-Yu Lin , Brian Daly , Ze-Qing Chen , Hannah S.N. Crory , H. Q. Nimal Gunaratne , Eric V. Anslyn , A. Prasanna de Silva
{"title":"Shape-shifting p-cyclophanes as portals to switching, sensing, delivery and logic operations in water†","authors":"Chao-Yi Yao ,&nbsp;Hong-Yu Lin ,&nbsp;Brian Daly ,&nbsp;Ze-Qing Chen ,&nbsp;Hannah S.N. Crory ,&nbsp;H. Q. Nimal Gunaratne ,&nbsp;Eric V. Anslyn ,&nbsp;A. Prasanna de Silva","doi":"10.1039/d2qo02043b","DOIUrl":"10.1039/d2qo02043b","url":null,"abstract":"<div><p>The hybridization state of carbon atoms between phenylene units in <em>p</em>-cyclophanes is shown to control the guest binding properties of these hosts. Dimeric cyclophanes can be shape-switched by redox so that small aromatics can be captured or released. Trimeric cyclophanes perform similar functions on polypyridineRu(<span>ii</span>) complexes. Controlled capture and release are key to delivery of such cargos. The luminescence and electrochemical signals which are modulated during these processes serve as sensing functions. Some of these modulations are so strong that Boolean logic schemes can be applied. Small-scale serial integration of sequential and combinational logic is seen.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 6","pages":"Pages 1570-1576"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3864530","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: 1
Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism 吡啶1，n-两性离子（n=4和5）环化反应的最新进展：范围和机理
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00228d
Jiali Huang , Lei Zhang , Xiangtai Meng
{"title":"Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism","authors":"Jiali Huang ,&nbsp;Lei Zhang ,&nbsp;Xiangtai Meng","doi":"10.1039/d3qo00228d","DOIUrl":"10.1039/d3qo00228d","url":null,"abstract":"<div><p>Nitrogen- and sulfur-containing heterocyclic compounds widely exist in bioactive natural products and drug molecules with unique bioactivity. In the past few decades, great efforts have been devoted to developing convenient and efficient strategies for the synthesis of these compounds. Pyridinium zwitterions with unique reactivity play a significant role in the construction of nitrogen- and sulfur-containing heterocycles. In recent years, pyridinium zwitterions have been extensively used in cyclization reactions for the synthesis of novel heterocyclic compounds. This review summarizes the recent advances in cyclization reactions involving pyridinium 1,<em>n</em>-zwitterions (<em>n</em> = 4 and 5) and highlights the applications of these zwitterions in the efficient construction of heterocycles.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 11","pages":"Pages 2813-2829"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3864552","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: 1
Ligand-assisted olefin-switched divergent oxidative Heck cascade with molecular oxygen enabled by self-assembled imines† 配体辅助的烯烃与自组装亚胺实现的分子氧切换发散氧化Heck级联†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00316g
Bairong Liu , Jianhang Rao , Weibing Liu , Yang Gao , Yanping Huo , Qian Chen , Xianwei Li
{"title":"Ligand-assisted olefin-switched divergent oxidative Heck cascade with molecular oxygen enabled by self-assembled imines†","authors":"Bairong Liu ,&nbsp;Jianhang Rao ,&nbsp;Weibing Liu ,&nbsp;Yang Gao ,&nbsp;Yanping Huo ,&nbsp;Qian Chen ,&nbsp;Xianwei Li","doi":"10.1039/d3qo00316g","DOIUrl":"10.1039/d3qo00316g","url":null,"abstract":"<div><p>Divergent oxidative Heck reaction has proven to be reliable for the rapid construction of molecular complexity, while olefins switched the outcome that remained underexplored. Herein, olefins tuned the divergent oxidative Heck reaction with O<sub>2</sub>, enabled by self-assembled imines, which was achieved with site selectivity and stereoselectivity. The compatiblity of strongly coordinating pyridines and quinolines enabled the concise delivery of a selective serotonin 4 receptor ligand, topotecan, and irinotecan analogues.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2128-2137"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3840393","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
Controllable carbonyl-assisted C(sp3)–C(sp3) bond reduction and reorganization† 可控羰基辅助的C（sp3）–C（sp三）键还原和重组†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01981g
Shengke Wang , Yitu Wang , Kun Hu , Kai Wang , Xigeng Zhou
{"title":"Controllable carbonyl-assisted C(sp3)–C(sp3) bond reduction and reorganization†","authors":"Shengke Wang ,&nbsp;Yitu Wang ,&nbsp;Kun Hu ,&nbsp;Kai Wang ,&nbsp;Xigeng Zhou","doi":"10.1039/d2qo01981g","DOIUrl":"10.1039/d2qo01981g","url":null,"abstract":"<div><p>C–C bond reduction and reorganization are fundamentally important in organic synthesis. However, there are no practical methods for tandem C–C reduction and reorganization. Here we report a versatile approach for selective reduction of the unstrained C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bond of ketones, including hydrogenolytic [2 + 2 + 2]-cycloreversion of 2,4-diaroylcyclohexanols, without requiring protecting groups or hydrogen gas. Mechanistic data demonstrate that the C–C cleavage occurs <em>via</em> a bimetallic pathway, and nucleophile trapping of the resulting enone is crucial for C–C reduction relay. Moreover, a practical strategy for intramolecular C–C cascade reorganization is established <em>via</em> iterative retro-Michael/intramolecular Michael addition sequence, thus enabling cyclizative degradation of poly(vinylketone) to trisubstituted cyclohexanes. These results could open new prospects for unstrained C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bond disconnection and reconstruction.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2234-2242"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3840409","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