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Photochemical akynylperfluoroalkylation of unactive alkenes mediated by halogen-bonded charge-transfer complexes† 卤素键电荷转移配合物介导的非活性烯烃的光化学全氟烷基化反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00304c
Huangbin Sun , Chang Huang , Xueting Bin , Fuzhi Cui , Guofang Jiang
{"title":"Photochemical akynylperfluoroalkylation of unactive alkenes mediated by halogen-bonded charge-transfer complexes†","authors":"Huangbin Sun ,&nbsp;Chang Huang ,&nbsp;Xueting Bin ,&nbsp;Fuzhi Cui ,&nbsp;Guofang Jiang","doi":"10.1039/d3qo00304c","DOIUrl":"10.1039/d3qo00304c","url":null,"abstract":"<div><p>We describe a catalyst-free visible-light mediated akynylperfluoroalkylation of unactive alkenes with perfluoroalkyl iodides, which provides a series of α-perfluoroalkyl-β-alkynyl ketone derivatives. This new synthetic protocol is enabled by a charge-transfer complex, which is a compound of a 1,4-enynol anion and an enolate ion of acetone as the electron donor and perfluoroalkyl iodides as the electron acceptor. Excellent functional group compatibility and chemoselectivity render this method suitable for fluoroalkylation of pharmaceutically relevant molecules, featuring a broad substrate scope, scalability and significant characteristics of green chemistry, further demonstrating the flexibility and potential for the synthesis of the mentioned compounds.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2332-2339"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934882","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: 2
Methylene-bridged naphthotubes: new macrocyclic arenes with great potential for supramolecular chemistry† 亚甲基桥接萘管:具有巨大超分子化学潜力的新型大环芳烃
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00258f
Miaomiao Yan , Jiong Zhou
{"title":"Methylene-bridged naphthotubes: new macrocyclic arenes with great potential for supramolecular chemistry†","authors":"Miaomiao Yan ,&nbsp;Jiong Zhou","doi":"10.1039/d3qo00258f","DOIUrl":"10.1039/d3qo00258f","url":null,"abstract":"<div><p>Macrocyclic arenes have been widely used due to their special structures, ease of modification, and outstanding properties. However, macrocyclic arenes with well-defined cavities are still rare. Recently, Quan, Jiang and co-workers constructed a novel class of macrocyclic arenes with well-defined cavities, namely methylene-bridged naphthotubes, which used rigid and curved alkoxy-substituted bisnaphthalene clefts as building blocks. Compared with structurally similar but flexible macrocycles, methylene-bridged naphthotubes possessed stronger binding affinities to organic cations and showed more outstanding molecular recognition capabilities. Moreover, methylene-bridged naphthotubes could serve as chiral sensors for chiral organic cations through different chiral transfer mechanisms. Herein, we highlight this ground-breaking work, which opens up great prospects for the unlimited application of macrocyclic arenes with well-defined cavities in supramolecular chemistry.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2340-2345"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934883","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: 4
Dual nickel/photoredox catalyzed carboxylation of C(sp2)-halides with formate† 双镍/光氧化还原催化C(sp2)-卤化物与甲酸†的羧化反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01361d
Ming-Chen Fu , Jia-Xin Wang , Wei Ge , Fang-Ming Du , Yao Fu
{"title":"Dual nickel/photoredox catalyzed carboxylation of C(sp2)-halides with formate†","authors":"Ming-Chen Fu ,&nbsp;Jia-Xin Wang ,&nbsp;Wei Ge ,&nbsp;Fang-Ming Du ,&nbsp;Yao Fu","doi":"10.1039/d2qo01361d","DOIUrl":"10.1039/d2qo01361d","url":null,"abstract":"<div><p>Herein, we report an efficient and practical protocol for dehalocarboxylation of C(sp<sup>2</sup>)-halides with formate by the engagement of a CO<sub>2</sub> radical anion in a nickel-mediated bond-forming process. A wide variety of aryl iodides, aryl bromides, and alkenyl bromides bearing a diverse set of functional groups underwent the reaction smoothly through visible-light photoredox nickel dual catalysis. The synthesis of several <sup>13</sup>C-labeled drug intermediates and the gram-scale synthesis of commercial drugs highlight the synthetic value of the approach in drug discovery settings.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 1","pages":"Pages 35-41"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934894","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: 3
Site-selective carbamoylation of carbohydrates catalyzed by SnCl2/Me2SnCl2 leading to complementary selectivity† SnCl2/Me2SnCl2催化碳水化合物的位点选择性氨基化，导致互补选择性†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00607g
Yang-Fan Guo , Tao Luo , Hai Dong
{"title":"Site-selective carbamoylation of carbohydrates catalyzed by SnCl2/Me2SnCl2 leading to complementary selectivity†","authors":"Yang-Fan Guo ,&nbsp;Tao Luo ,&nbsp;Hai Dong","doi":"10.1039/d3qo00607g","DOIUrl":"10.1039/d3qo00607g","url":null,"abstract":"<div><p>This work reports SnCl<sub>2</sub>/Me<sub>2</sub>SnCl<sub>2</sub>-catalyzed site-selective carbamoylation of carbohydrates with a broad substrate scope, associated with mild reaction conditions, good selectivity and high isolated yields (using a flash column). In particular, the selectivity of carbamoylation resulting from the SnCl<sub>2</sub> method is complementary to that resulting from the Me<sub>2</sub>SnCl<sub>2</sub> method in many cases. For several glycoside substrates containing <em>cis</em>-diol, their axial hydroxyl groups are selectively carbamoylated in the presence of the SnCl<sub>2</sub> catalyst, while their equatorial hydroxyl groups are selectively carbamoylated in the presence of the Me<sub>2</sub>SnCl<sub>2</sub> catalyst. The substrate scope for the SnCl<sub>2</sub> method also includes glycosides containing 1,3-diol, but excludes glycosides containing <em>trans</em>-diol. The substrate scope for the Me<sub>2</sub>SnCl<sub>2</sub> method can include glycosides containing <em>trans</em>-diol.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 14","pages":"Pages 3553-3558"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934896","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
The α-alkylation of carbonyl sulfoxonium ylides: studies and applications in the synthesis of new sulfur heterocycles† 羰基亚砜鎓化物的α-烷基化:在新型硫杂环合成中的研究与应用
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00688c
Matheus P. de Jesus , Radell Echemendía , Antonio C.B. Burtoloso
{"title":"The α-alkylation of carbonyl sulfoxonium ylides: studies and applications in the synthesis of new sulfur heterocycles†","authors":"Matheus P. de Jesus ,&nbsp;Radell Echemendía ,&nbsp;Antonio C.B. Burtoloso","doi":"10.1039/d3qo00688c","DOIUrl":"10.1039/d3qo00688c","url":null,"abstract":"<div><p>The challenging direct α-alkylation of sulfoxonium ylides is demonstrated after a deep study with several electrophiles. Twenty-five alkylated ester sulfoxonium ylides could be prepared in 12–67% isolated yields, employing Michael acceptors as electrophiles. Interestingly, no product arising from the classical cyclopropanation reaction, commonly observed for the reaction between sulfur ylides and Michael acceptors, was observed. To demonstrate the applicability of these unprecedented and more decorated sulfoxonium ylides, new and medicinal-chemistry important sulfur heterocycles, such as 2-mercaptobenzothiazoles, 1,4-benzothiazin-3-ones, and coumarin derivatives, were prepared.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 14","pages":"Pages 3577-3584"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934900","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
Dual role of BrCF2CO2Et: difluorocarbene-enabled access to α-trifluoromethyl ketones from sulfoxonium ylides† BrCF2CO2Et的双重作用：二氟卡宾能够从亚磺酰亚砜中获得α-三氟甲基酮†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00609c
Chun-Yan Wu , Xiang-Long Chen , Huai-Yu Wang , Dong-Sheng Yang , Shi-Yi Zhuang , You Zhou , Zhi-Cheng Yu , Yan-Dong Wu , Xiao Geng , An-Xin Wu
{"title":"Dual role of BrCF2CO2Et: difluorocarbene-enabled access to α-trifluoromethyl ketones from sulfoxonium ylides†","authors":"Chun-Yan Wu ,&nbsp;Xiang-Long Chen ,&nbsp;Huai-Yu Wang ,&nbsp;Dong-Sheng Yang ,&nbsp;Shi-Yi Zhuang ,&nbsp;You Zhou ,&nbsp;Zhi-Cheng Yu ,&nbsp;Yan-Dong Wu ,&nbsp;Xiao Geng ,&nbsp;An-Xin Wu","doi":"10.1039/d3qo00609c","DOIUrl":"10.1039/d3qo00609c","url":null,"abstract":"<div><p>A transition metal and external fluorine anion-free method has been developed for the efficient trifluoromethylation of sulfoxonium ylides with BrCF<sub>2</sub>CO<sub>2</sub>Et to afford α-trifluoromethyl ketones. Mechanistic investigation revealed that taking advantage of the dual role of BrCF<sub>2</sub>CO<sub>2</sub>Et, which concurrently acts as a CF<sub>2</sub> and F source, is key to realizing this reaction. This method is applicable to the late-stage modification of biologically active compounds and can be readily scaled up.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3741-3745"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830503","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
Palladium-catalyzed decarboxylation [2 + 2 + 2] annulation approach to chromone-containing polycyclic compounds† 钯催化脱羧[2+2+2]环化方法制备含色酮的多环化合物†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00764b
Yu-Chen Fang , Jia-He Chen , Ren-Feng Xiu , Li-Ren Zhang , Fang-Hua Zheng , Yong-Zheng Chen , Zi-Wei Gao , Wen-Yong Han
{"title":"Palladium-catalyzed decarboxylation [2 + 2 + 2] annulation approach to chromone-containing polycyclic compounds†","authors":"Yu-Chen Fang ,&nbsp;Jia-He Chen ,&nbsp;Ren-Feng Xiu ,&nbsp;Li-Ren Zhang ,&nbsp;Fang-Hua Zheng ,&nbsp;Yong-Zheng Chen ,&nbsp;Zi-Wei Gao ,&nbsp;Wen-Yong Han","doi":"10.1039/d3qo00764b","DOIUrl":"10.1039/d3qo00764b","url":null,"abstract":"<div><p>We present herein a palladium-catalyzed decarboxylation [2 + 2 + 2] annulation with 3-iodochromones, bridged olefins, and <em>o</em>-bromobenzoic acids to give various <em>exo</em>-chromone-containing polycyclic compounds (49 examples, up to 92% yield), in which <em>o</em>-bromobenzoic acids were employed as the electrophilic aryl units. Gram-scale experiments, late-stage modification of estrone, and further transformations of products show a great potential of this palladium-catalyzed Heck coupling/C(sp<sup>2</sup>)–H activation/decarboxylation cascade for drug discovery and development.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3752-3759"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830505","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
Mechanistic investigation of the transfer hydrogenation of alkynes catalysed by an MLC catalyst with multiple ancillary ligand sites† 具有多个辅助配体位点的MLC催化剂催化炔烃转移加氢的机理研究†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00575e
Yuan Zhang , Lan-Yu Li , Cheng Hou
{"title":"Mechanistic investigation of the transfer hydrogenation of alkynes catalysed by an MLC catalyst with multiple ancillary ligand sites†","authors":"Yuan Zhang ,&nbsp;Lan-Yu Li ,&nbsp;Cheng Hou","doi":"10.1039/d3qo00575e","DOIUrl":"10.1039/d3qo00575e","url":null,"abstract":"This study reveals the mechanistic details of the transfer hydrogenation catalyzed by an MLC catalyst with multiple ancillary ligand sites.","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3766-3775"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830508","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
Silver-catalysed [3 + 2] annulation reaction of aryldiazonium salts with allenes enabled by boronate direction† 硼离子方向使芳基重氮盐与烯烯的银催化[3 + 2]环化反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01585d
Xing Peng , Meng-Meng Zheng , Pei Qin , Xiao-Song Xue , Fa-Guang Zhang , Jun-An Ma
{"title":"Silver-catalysed [3 + 2] annulation reaction of aryldiazonium salts with allenes enabled by boronate direction†","authors":"Xing Peng ,&nbsp;Meng-Meng Zheng ,&nbsp;Pei Qin ,&nbsp;Xiao-Song Xue ,&nbsp;Fa-Guang Zhang ,&nbsp;Jun-An Ma","doi":"10.1039/d2qo01585d","DOIUrl":"10.1039/d2qo01585d","url":null,"abstract":"<div><p>Allenes are a unique type of powerful synthon used for the construction of various carbocycles and heterocycles, but their annulation reactions with N–N triple bond electrophiles have not been disclosed. Here we report an efficient silver-catalysed boronate-directed [3 + 2] annulation reaction of aryl diazonium salts with allenylboronates. This transformation offers unprecedented access to a wide scope of <em>N</em><sup>1</sup>-aryl-1<em>H</em>-pyrazoles with high regioselectivities under mild conditions. Preliminary experimental and computational studies support a transmetalation/stepwise cycloaddition/pyrazolyl silver hydrolysis pathway involving propargyl silver species as the key intermediate in enabling reactivity and controlling regioselectivity.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 1","pages":"Pages 74-82"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830512","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
A ligand-enabled, copper(ii)-catalyzed, highly selective and efficient synthesis of 2E-alkenylfurans from ynenones† 配体使能、铜（ii）催化、高选择性和高效地从炔酮合成2E烯基呋喃†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01741e
Shao-Yu Zou , Fang Yang , Xin Zhao , Xin-Ge Ren , Zi-Sheng Chen , Kegong Ji
{"title":"A ligand-enabled, copper(ii)-catalyzed, highly selective and efficient synthesis of 2E-alkenylfurans from ynenones†","authors":"Shao-Yu Zou ,&nbsp;Fang Yang ,&nbsp;Xin Zhao ,&nbsp;Xin-Ge Ren ,&nbsp;Zi-Sheng Chen ,&nbsp;Kegong Ji","doi":"10.1039/d2qo01741e","DOIUrl":"10.1039/d2qo01741e","url":null,"abstract":"<div><p>We describe a ligand-enabled Cu(<span>ii</span>)-catalyzed approach for highly selective synthesis of 2<em>E</em>-alkenylfurans <strong>2</strong> from ynenones under an air atmosphere. In this reaction, the amide group on our designed 1,10-phenanthroline framework had a key role in promoting the α-H internal 1,2-migration to Cu(<span>ii</span>) carbene species and stabilizing the <em>in situ</em>-generated carbocation. This approach prevented the external oxygen participating to oxidize α-furyl copper carbene rapidly to 2-acylfuran. With the bifunctional ligand <strong>L1</strong>, the Cu(<span>ii</span>) catalyst became highly efficient at catalyzing ynenones selective to 2<em>E</em>-alkenylfurans <strong>2</strong> under an air atmosphere at room temperature in excellent yields. Moreover, the ligand could lower the Cu(<span>ii</span>) catalyst loading dramatically to ppm-level at a higher temperature and concentration, with turnover numbers of the Cu(<span>ii</span>) catalyst up to 9300. This economical and practical approach with good application was mild and environmentally friendly.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 3","pages":"Pages 767-773"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830515","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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