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Synthesis of α-amino acid derived (1,2,3-triazol-4-yl)-picolinamide (tzpa) ligands and their corresponding luminescent Tb(iii) complexes† α-氨基酸衍生的（1,2,3-三唑-4-基）-吡啶酰胺（tzpa）配体及其相应发光Tb（iii）配合物的合成†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00232b
Isabel N. Hegarty , Chris S. Hawes , Thorfinnur Gunnlaugsson
{"title":"Synthesis of α-amino acid derived (1,2,3-triazol-4-yl)-picolinamide (tzpa) ligands and their corresponding luminescent Tb(iii) complexes†","authors":"Isabel N. Hegarty ,&nbsp;Chris S. Hawes ,&nbsp;Thorfinnur Gunnlaugsson","doi":"10.1039/d3qo00232b","DOIUrl":"10.1039/d3qo00232b","url":null,"abstract":"<div><p>The synthesis of chiral α-amino acid derived (1,2,3-triazol-4-yl)-picolinamide (<strong>tzpa</strong>) ligands <strong>4–6</strong> designed by combining the coordination properties of two well-known ligand structures within a single unit is described. The self-assembly formation between these ligands and the lanthanide ion Tb(<span>iii</span>) was investigated in solution by probing the ground and the singlet excited state properties of the ligands as well as monitoring the evolution of the Tb(<span>iii</span>) emission at long wavelengths. The spectroscopic results showed that while under thermodynamic control the 1 : 3 (Tb : L) is produced, then analysis of the titration data using non-liner regression analysis demonstrated that the main species in solution is the 1 : 2 (Tb : L) after the addition of 0.5 equivalents of Tb(<span>iii</span>).</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 8","pages":"Pages 1915-1926"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3646305","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
Metal-free heteroarene C(sp2)–H amination with unprotected (hetero)arylamines† 不含金属的杂芳烃C（sp2）-H与无保护的（杂）芳酰胺的胺化†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00338h
Tao Wen , Zhen Zhang , Lihua Ye , Chihong Zhang , Bo Jin , Wenkun Wang , Zhong-Ning Chen , Hu Cai
{"title":"Metal-free heteroarene C(sp2)–H amination with unprotected (hetero)arylamines†","authors":"Tao Wen ,&nbsp;Zhen Zhang ,&nbsp;Lihua Ye ,&nbsp;Chihong Zhang ,&nbsp;Bo Jin ,&nbsp;Wenkun Wang ,&nbsp;Zhong-Ning Chen ,&nbsp;Hu Cai","doi":"10.1039/d3qo00338h","DOIUrl":"10.1039/d3qo00338h","url":null,"abstract":"<div><p>Regioselective functionalization of C–H bonds has attracted the attention of chemists in recent years. However, transition metals are often expensive and indispensable in most C–H activation reactions. Here, we describe a metal-free intramolecular heteroarene C(sp<sup>2</sup>)–H amination from unprotected (hetero)arylamines. Exposure of 2-(pyridin-3-yl)aniline to potassium <em>tert</em>-butoxide was found to access <em>N</em>-heterocycles without additives, which unlocks a new breakthrough. This process is involved in the synthesis of a wide variety of <em>N</em>-heterocycles including natural products and bioactive compounds. Mechanistic studies have established that these reactions proceed through an S<sub>N</sub>ArH process. Such a unique transformation opens the door toward the regioselective intramolecular C–H amination of weakly reactive arylamines with heterocyclic compounds.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 3045-3051"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3646310","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
Iron-catalyzed cross-electrophile coupling of bromostyrenes and chlorosilanes† 铁催化的溴苯乙烯与氯硅烷的交叉亲电偶联
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00372h
Ying Lin , Liang Zou , Renren Bai , Xiang-Yang Ye , Tian Xie , Yang Ye
{"title":"Iron-catalyzed cross-electrophile coupling of bromostyrenes and chlorosilanes†","authors":"Ying Lin ,&nbsp;Liang Zou ,&nbsp;Renren Bai ,&nbsp;Xiang-Yang Ye ,&nbsp;Tian Xie ,&nbsp;Yang Ye","doi":"10.1039/d3qo00372h","DOIUrl":"10.1039/d3qo00372h","url":null,"abstract":"<div><p>We report here a facile and efficient vinylation method using Fe-catalyzed cross-electrophile coupling of readily available vinyl- and hydro-chlorosilanes with a variety of substituted alkenyl bromides using manganese as the terminal reductant. This C(sp<sup>2</sup>)–Si forming modular approach shows excellent functional group tolerance and broad substrate scope, which allows the creation of a series of vinyl organosilanes, including electron-rich, electron-poor, and <em>ortho</em>-/<em>meta</em>-/<em>para</em>-substituted vinyl electrophiles, which were coupled successfully. Moreover, several substrates with structurally complex natural products and pharmaceutical motifs were well modified by this vinyl silylation process. Gram-scale reaction and derivatization of the formed vinyl organosilanes are demonstrated.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 3052-3060"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3646311","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
A strategy for regioselective B–H functionalization of o-carboranes via base metal catalysis 碱金属催化邻碳硼烷区域选择性B–H功能化的策略
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00621b
Jie Zhang , Zuowei Xie
{"title":"A strategy for regioselective B–H functionalization of o-carboranes via base metal catalysis","authors":"Jie Zhang ,&nbsp;Zuowei Xie","doi":"10.1039/d3qo00621b","DOIUrl":"10.1039/d3qo00621b","url":null,"abstract":"<div><p>Carboranes, a class of carbon–boron molecular clusters, have unique characteristics and are finding a variety of applications ranging from materials to medicine. In this connection, selective functionalization of <em>o</em>-carboranes has attracted enormous research interest, particularly in regio- and enantio-selective cage B–H derivatization among ten chemically similar BH vertices in <em>o</em>-carboranes. Over the years, precious transition metal-catalyzed cage B–H functionalization has made significant advances in the preparation of diversely functionalized <em>o</em>-carboranes. In contrast, research on B–H functionalization <em>via</em> a base metal catalysis strategy has just begun recently. This paper summarizes the recent developments in base metal-catalyzed regioselective B–H functionalization of carboranes.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 3074-3079"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3646314","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
Recent advances in the asymmetric catalytic construction of oxa-quaternary carbon centers 不对称催化构建氧杂季碳中心的研究进展
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00527e
Yu-Ping He , Di Tian , Xing-Zi Li , Hua Wu
{"title":"Recent advances in the asymmetric catalytic construction of oxa-quaternary carbon centers","authors":"Yu-Ping He ,&nbsp;Di Tian ,&nbsp;Xing-Zi Li ,&nbsp;Hua Wu","doi":"10.1039/d3qo00527e","DOIUrl":"10.1039/d3qo00527e","url":null,"abstract":"<div><p>Compounds bearing oxa-quaternary carbon centers, such as chiral tertiary alcohols, ethers, esters, and acetals, are widely found in a number of bioactive compounds, natural products, agrochemicals and drugs. Besides, they could also serve as privileged building blocks in organic synthesis, especially in a series of bond-forming transformations. Alternatively, among these compounds, enantiomerically pure tertiary alcohols have been extensively used to develop new chiral ligands for a range of organic transformations based on their inherent rigidity and bulky three-dimensional environment. Therefore, developing efficient strategies for the enantioselective catalytic synthesis of these compounds has been of long-standing interest among the chemical and pharmaceutical communities for decades. In contrast to chiral oxa-tertiary stereocenters, the construction of enantioenriched oxa-quaternary carbon centers remains a great challenge in asymmetric synthesis due to the less reactive nature of their precursors and the decreased enantioface differentiation between the two substituents at the prochiral carbon center. Although several tutorial reviews on the asymmetric synthesis of chiral compounds bearing quaternary stereocenters have appeared, there is no specialized review that summarizes the content of enantioselective construction of oxa-quaternary stereocenters. Due to the rapid development in this research field, a timely summarization of the recent achievements is highly valuable. This review exclusively focuses on the recent advances (from 2020 to the beginning of 2023) in asymmetric reactions for the synthesis of enantiomerically pure compounds bearing oxa-quaternary stereocenters.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 3110-3129"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3646317","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
Asymmetric synthesis of cyclopenta[b]indoles via organocatalytic formal (3 + 2) cyclization of β-keto ester with azonaphthalene† β-酮酯与偶氮萘的有机催化形式（3+2）环化不对称合成环戊二烯[b]吲哚†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00306j
Yanji Song , Shi Tang , Qianping Chen , Qingfa Tan , Weidi Cao , Xiaoming Feng , Xiaohua Liu
{"title":"Asymmetric synthesis of cyclopenta[b]indoles via organocatalytic formal (3 + 2) cyclization of β-keto ester with azonaphthalene†","authors":"Yanji Song ,&nbsp;Shi Tang ,&nbsp;Qianping Chen ,&nbsp;Qingfa Tan ,&nbsp;Weidi Cao ,&nbsp;Xiaoming Feng ,&nbsp;Xiaohua Liu","doi":"10.1039/d3qo00306j","DOIUrl":"10.1039/d3qo00306j","url":null,"abstract":"<div><p>Enantioselective formal (3 + 2) cyclization of cyclic β-keto esters with azonaphthalenes has been established. A range of cyclopenta[<em>b</em>]indoles have been synthesized in good yields (up to 99% yield) with high diastereo- and enantioselectivity (up to 96% ee, &gt;19 : 1 dr) by using guanidine-amides as catalysts under mild reaction conditions. A bifunctional hydrogen-bond activation model was rationalized for the origin of enantioselectivity.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 11","pages":"Pages 2734-2739"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3864541","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
Dirhodium: carbene transformations and beyond Dirhodium：卡宾转化及其超越
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00400g
Rui Wu , Dong Zhu , Shifa Zhu
{"title":"Dirhodium: carbene transformations and beyond","authors":"Rui Wu ,&nbsp;Dong Zhu ,&nbsp;Shifa Zhu","doi":"10.1039/d3qo00400g","DOIUrl":"10.1039/d3qo00400g","url":null,"abstract":"<div><p>Dirhodiums, which feature lantern- or paddlewheel-like structures, have emerged as a class of useful catalysts in organic synthesis. Among the transformations catalyzed by dirhodiums, the carbene, with diazo, cyclopropene, hydrazone and triazole as the precursors, and nitrene transfer reactions are dominant and have reached remarkable levels of efficiency and selectivity. Additionally, more and more fascinating properties of dirhodium have been explored and discovered in the past few decades, which has accelerated the applications of dirhodium in organic synthesis. In this review, we aim to showcase these advances in dirhodium-catalyzed transformations. The transformations including cycloisomerization, hetero-Diels–Alder (HDA) reactions, ene reactions, arylation, radical oxidation reactions and C–H activation, <em>etc</em>. will be covered. In these reactions, the dirhodiums could not only work as redox-neutral catalysts but also as redox catalysts.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 11","pages":"Pages 2849-2878"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3864554","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
Ratiometric sensing of β-galactosidase based on excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement† 基于激发态分子内质子转移（ESIPT）和固态发光增强的β-半乳糖苷酶比值传感†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00605k
He Tian Jr. , Wei Lin , Xi-Le Hu , Jing-Bo Wang , Min-Yu Zhang , Yi Zang , Xin-Yan Wu , Jia Li , Tony D. James , Xiao-Peng He
{"title":"Ratiometric sensing of β-galactosidase based on excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement†","authors":"He Tian Jr. ,&nbsp;Wei Lin ,&nbsp;Xi-Le Hu ,&nbsp;Jing-Bo Wang ,&nbsp;Min-Yu Zhang ,&nbsp;Yi Zang ,&nbsp;Xin-Yan Wu ,&nbsp;Jia Li ,&nbsp;Tony D. James ,&nbsp;Xiao-Peng He","doi":"10.1039/d3qo00605k","DOIUrl":"10.1039/d3qo00605k","url":null,"abstract":"<div><p>Glycosidases play important roles in modulating the structural and functional integrity of glycoproteins and glycolipids, and thus are promising biomarkers for disease diagnosis. While current approaches for glycosidase detection mainly rely on an enhancement of the UV-vis absorbance or fluorescence emission of glycosyl indicators, here we develop a ratiometric fluorescent probe for the sensitive and selective detection of glycosidase activity based on the combined mechanisms of excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement (SSLE). The probe behaves like a typical SSLE when glycosylated, and exhibits a ∼140<!--> <!-->nm red-shift in fluorescence owing to activation of ESIPT after deglycosylation. Such a large Stokes shift may facilitate the unbiased analysis of glycosidase activities when used in diagnostic and drug-screening assays.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 2913-2917"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3864558","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
Facile access to 1-aryl-2,3-naphthalimides via consecutive amidation/dehydro-Diels–Alder reactions† 通过连续的酰胺化/脱氢Diels-Alder反应促进1-芳基-2,3-邻苯二甲酰亚胺的获取†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00395g
Chaoyang Song , Tingwei Shen , Lingzhu Chen , Tingting Li
{"title":"Facile access to 1-aryl-2,3-naphthalimides via consecutive amidation/dehydro-Diels–Alder reactions†","authors":"Chaoyang Song ,&nbsp;Tingwei Shen ,&nbsp;Lingzhu Chen ,&nbsp;Tingting Li","doi":"10.1039/d3qo00395g","DOIUrl":"10.1039/d3qo00395g","url":null,"abstract":"<div><p>A facile approach for quick and efficient access to structurally complex 2,3-naphthalimide derivatives is developed. Easily accessible and inexpensive β-arylpropiolic acids and primary amines are used as the reaction starting materials. Both reactants can tolerate a diversity of substituents with various electronic and steric effects. Multi-functional 1-aryl-2,3-naphthalimides are afforded in generally moderate to excellent yields through a consecutive cascade amidation/dehydro-Diels–Alder reaction in one-pot operations. Promising applications of the afforded 1-aryl-2,3-naphthalimide products in bactericide development for plant protections are also exhibited.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3792-3798"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3865620","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
Photocatalyzed alkoxycarbonylmethylation of pyridines with α-diazoacetates† 吡啶与α-重氮乙酸盐的光催化烷氧羰基甲基化†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01818g
Haisheng Xie , Zhongfeng Luo , Fengjuan Chen , Huanfeng Jiang , Wei Zeng
{"title":"Photocatalyzed alkoxycarbonylmethylation of pyridines with α-diazoacetates†","authors":"Haisheng Xie ,&nbsp;Zhongfeng Luo ,&nbsp;Fengjuan Chen ,&nbsp;Huanfeng Jiang ,&nbsp;Wei Zeng","doi":"10.1039/d2qo01818g","DOIUrl":"10.1039/d2qo01818g","url":null,"abstract":"<div><p>A photocatalyzed regioselective alkoxycarbonylmethylation of 2-aminopyridines with α-diazoacetates has been developed. This method provides a metal-free strategy to assemble 2-aryl-2-pyridylacetic esters <em>via</em> a direct pyridyl Csp<sup>2</sup>–H bond carbenoid insertion under mild conditions.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 5","pages":"Pages 1270-1274"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3829666","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
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