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Supramolecular vesicle engineering by regulating the assembly of shape-persistent aromatic-hydrazone macrocycles† 通过调节形状持久的芳香腙大环的组装进行超分子囊泡工程†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01691e
He Deng , Guanfei Gong , Siheng Lv , Yi Chen , Qi Zhao , Shanshan Liu , Shigui Chen , Lu Wang
{"title":"Supramolecular vesicle engineering by regulating the assembly of shape-persistent aromatic-hydrazone macrocycles†","authors":"He Deng ,&nbsp;Guanfei Gong ,&nbsp;Siheng Lv ,&nbsp;Yi Chen ,&nbsp;Qi Zhao ,&nbsp;Shanshan Liu ,&nbsp;Shigui Chen ,&nbsp;Lu Wang","doi":"10.1039/d2qo01691e","DOIUrl":"10.1039/d2qo01691e","url":null,"abstract":"<div><p>Size is an important factor for vesicles, which is essential for their application, particularly in nanomedicine and nanomaterials. Unlike polymer vesicles, whose size can be controlled by the hydrophobic/hydrophilic content or the chain length, the size of supramolecular vesicles mainly depends on the assembly of the supramolecular building blocks. Herein, we describe a novel method to manipulate the size of supramolecular vesicles by regulating the assembly of hydrogen-bonding aromatic hydrazone macrocycles with different pyridinium guests. The assembly of an aromatic hydrazone macrocycle with different mono-/bi-pyridinium guests is confirmed by <sup>1</sup>H NMR, DOSY, MS, and TEM. This study offers a new strategy to manipulate the size of supramolecular vesicles, which might be of importance for the application of vesicles.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 2","pages":"Pages 317-326"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3646319","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
An alternative metal-free amination approach to 3-trifluoromethyl aniline derivatives: the major products under Kröhnke pyridine synthesis conditions† 3-三氟甲基苯胺衍生物的另一种无金属胺化方法：Kröhnke吡啶合成条件下的主要产物†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00493g
Zheng Fang , Biqiong Hong , Wei Wu , Zhiqiang Weng
{"title":"An alternative metal-free amination approach to 3-trifluoromethyl aniline derivatives: the major products under Kröhnke pyridine synthesis conditions†","authors":"Zheng Fang ,&nbsp;Biqiong Hong ,&nbsp;Wei Wu ,&nbsp;Zhiqiang Weng","doi":"10.1039/d3qo00493g","DOIUrl":"10.1039/d3qo00493g","url":null,"abstract":"<div><p>As an alternative metal-free amination, we report a simple and efficient annulation reaction of 1-(3,3,3-trifluoro-2-oxopropyl)pyridin-1-ium bromide and α,β-unsaturated carbonyl compounds with NH<sub>4</sub>OAc or amines. With the developed protocol, a series of 3-trifluoromethyl aniline derivatives as the major products were obtained in good to excellent yields under Kröhnke pyridine synthesis conditions. The reaction proceeds <em>via</em> a cascade process involving the 1,4-Michael addition of the pyridinium ylide to an α,β-unsaturated carbonyl compound, followed by intramolecular addition of a carbanion to the keto carbonyl group to form a dienone intermediate.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 13","pages":"Pages 3207-3212"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3646323","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
Mechanism of Co(iii)-catalyzed annulation of N-chlorobenzamide with styrene and origin of cyclopentadienyl ligand-controlled enantioselectivity† Co（iii）催化N-氯苯甲酰胺与苯乙烯环化的机理和环戊二烯基配体的来源控制的对映选择性†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00038a
Han Gao , Wujie Wang , Xiangying Lv , Gang Lu , Yuliang Li
{"title":"Mechanism of Co(iii)-catalyzed annulation of N-chlorobenzamide with styrene and origin of cyclopentadienyl ligand-controlled enantioselectivity†","authors":"Han Gao ,&nbsp;Wujie Wang ,&nbsp;Xiangying Lv ,&nbsp;Gang Lu ,&nbsp;Yuliang Li","doi":"10.1039/d3qo00038a","DOIUrl":"10.1039/d3qo00038a","url":null,"abstract":"<div><p>The mechanism of Co(<span>iii</span>)-catalyzed annulation of <em>N</em>-chlorobenzamide with styrene was computationally studied and the effects of chiral cyclopentadienyl (Cp) ligands on enantioselectivity were investigated by using energy decomposition analysis (EDA). The spin-crossover event of Co complexes is observed in the computed energy profile. The triplet state of Co species is favored in most of the intermediates and transition states except for the styrene migratory insertion step which prefers the singlet state. The irreversible styrene migratory insertion is the enantioselectivity-determining step of the reaction. EDA results indicate that the steric effect is the dominant factor for the high-level enantiocontrol, which highlights the importance of the additional bulky substituents on the Cp ring of trisubstituted BINOL-Cp ligands.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 7","pages":"Pages 1643-1650"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694162","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
Radical addition/spirocyclization cascade of tryptamine-derived isocyanides with aryl boronic acids: efficient access to spiroindoline derivatives† 色胺衍生的异氰酸酯与芳基硼酸的自由基加成/螺环化级联反应：有效获得螺吲哚啉衍生物†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01992b
Shuai Jiang , Yu-Xin Huang , Xiao-Feng Wang , Xiao-Ping Xu , Shun-Jun Ji
{"title":"Radical addition/spirocyclization cascade of tryptamine-derived isocyanides with aryl boronic acids: efficient access to spiroindoline derivatives†","authors":"Shuai Jiang ,&nbsp;Yu-Xin Huang ,&nbsp;Xiao-Feng Wang ,&nbsp;Xiao-Ping Xu ,&nbsp;Shun-Jun Ji","doi":"10.1039/d2qo01992b","DOIUrl":"10.1039/d2qo01992b","url":null,"abstract":"<div><p>An efficient Mn(<span>iii</span>)-promoted cascade reaction of tryptamine-derived isocyanides with arylboronic acids for accessing spiroindoline derivatives is described. The reaction proceeds <em>via</em> a radical addition/spirocyclization pathway, providing spiroindolines in good yields under mild conditions.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 7","pages":"Pages 1660-1668"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694164","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 reductive Sandmeyer-type reaction for the synthesis of sulfoxides from anilines under photocatalysis† 在光催化下由苯胺合成亚砜的还原Sandmeyer型反应†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00297g
Gangqi Peng , Hao Cheng , Xiya Cheng , Yang He , Yuanyuan An , Jie Wu , Danqing Zheng
{"title":"A reductive Sandmeyer-type reaction for the synthesis of sulfoxides from anilines under photocatalysis†","authors":"Gangqi Peng ,&nbsp;Hao Cheng ,&nbsp;Xiya Cheng ,&nbsp;Yang He ,&nbsp;Yuanyuan An ,&nbsp;Jie Wu ,&nbsp;Danqing Zheng","doi":"10.1039/d3qo00297g","DOIUrl":"10.1039/d3qo00297g","url":null,"abstract":"<div><p>A reductive Sandmeyer-type sulfinylation reaction of aryldiazonium salts with sodium sulfinates is reported. The reaction takes place under photocatalysis, generating a range of valuable sulfoxides <em>via</em> a radical substitution pathway. Aromatic amines can also be converted to the corresponding sulfoxides <em>via in situ</em> diazotization in a one-pot, two-step process. The late-stage sulfinylation of drug-based amines further demonstrated the practicality of this method.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 3033-3038"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694198","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
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
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