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Excited Pd-catalyzed dearomative 1,4-dicarbofunctionalization of nonactivated aromatic rings† 激发pd催化非活化芳香环的1,4-二碳功能化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-08 DOI: 10.1039/d4qo02173h
Kai Jiang , Ziyan Zhao , Xiaodong Yin , Fangjun Chen , Biaolin Yin
{"title":"Excited Pd-catalyzed dearomative 1,4-dicarbofunctionalization of nonactivated aromatic rings†","authors":"Kai Jiang ,&nbsp;Ziyan Zhao ,&nbsp;Xiaodong Yin ,&nbsp;Fangjun Chen ,&nbsp;Biaolin Yin","doi":"10.1039/d4qo02173h","DOIUrl":"10.1039/d4qo02173h","url":null,"abstract":"<div><div>Excited-palladium catalysis has already been exploited to achieve 1,4-difunctionalization of dienes <em>via</em> the radical generation of an allylpalladium intermediate. Herein, nonactivated phenyl rings, which can be treated as masked trienes, have accomplished dearomative 1,4-dicarbofunctionalization in an excited-palladium catalyzed two- or three-component reaction system. A wide range of alkyl bromides and 1,3-dicarbonyl compounds, playing the roles of radical precursors and nucleophiles, respectively, were found to be suitable for this reaction. Various three-dimensional molecular architectures with multiple quaternary carbon centers were efficiently constructed by means of this mild reaction.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1579-1585"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142936536","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 fluorinated dienes through hydrofluorination of 2-En-4-ynoates† 通过2-烯-4-炔酸酯的氢氟化获得氟化二烯
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-08 DOI: 10.1039/d4qo02049a
Yue Xia , Aaron D. Charlack , Rui Guo , Nicholas W. Wade , Yi-Ming Wang
{"title":"Access to fluorinated dienes through hydrofluorination of 2-En-4-ynoates†","authors":"Yue Xia ,&nbsp;Aaron D. Charlack ,&nbsp;Rui Guo ,&nbsp;Nicholas W. Wade ,&nbsp;Yi-Ming Wang","doi":"10.1039/d4qo02049a","DOIUrl":"10.1039/d4qo02049a","url":null,"abstract":"<div><div>The hydrofluorination of enynoates has been developed for the synthesis of fluorinated dienoates. Using a pyridinium tetrafluoroborate salt that is easily prepared on large scale, this approach enabled the direct conversion of these substrates to fluorinated targets through a vinyl cation mediated process. This approach was applied to a range of aryl-substituted enynoates to deliver the (<em>Z</em>)-configured products with high levels of stereo- and regioselectivity. Mechanistic studies were conducted to provide insights into the stereochemical outcome and reaction efficiency under different reaction conditions.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1425-1431"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d4qo02049a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841640","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
N-heterocyclic carbene-catalyzed decarboxylative cross-electrophile coupling to access sterically hindered ketones† n -杂环碳催化脱羧交叉亲电偶联获得立体受阻酮
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-08 DOI: 10.1039/d4qo02052a
Xiangyu Zhuang , Hao Li , Tingting Wang , Hongyu Wang , Bo Tang
{"title":"N-heterocyclic carbene-catalyzed decarboxylative cross-electrophile coupling to access sterically hindered ketones†","authors":"Xiangyu Zhuang ,&nbsp;Hao Li ,&nbsp;Tingting Wang ,&nbsp;Hongyu Wang ,&nbsp;Bo Tang","doi":"10.1039/d4qo02052a","DOIUrl":"10.1039/d4qo02052a","url":null,"abstract":"<div><div>Although radical NHC (nitrogen-heterocyclic carbene) catalysis has emerged as a powerful strategy for constructing carbon–carbon (C–C) bonds to generate value-added ketones from carbonyl compounds including carboxylic acids and aldehydes, great advances were generally focused on redox-neutral NHC catalysis and oxidative NHC catalysis until now. Cross-electrophile coupling reactions as powerful tools for forming C–C bonds avoiding using preformed carbon nucleophilic organometallic reagents have not been well developed by radical NHC catalysis. Here, we demonstrate that nitrogen-heterocyclic carbene (NHC), in conjunction with manganese (Mn), can promote the cross-coupling of aromatic acids or derivatives with a wide array of broadly available electrophiles to deliver various sterically bulky ketones with high yields. In addition, its utility in the concise synthesis of biologically active compounds is further highlighted.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1556-1564"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142917842","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
Superfast and highly selective water transport by hybrid aquapentamers incorporating a non-helicity codon† 含非螺旋密码子的杂化水七聚体的超快速和高选择性水传输
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-08 DOI: 10.1039/d4qo02231a
Gaiping Cao , Zihong Yang , Huaiqing Zhao , Jie Shen , Wenju Chang , Zhiwei Liu , Huaqiang Zeng
{"title":"Superfast and highly selective water transport by hybrid aquapentamers incorporating a non-helicity codon†","authors":"Gaiping Cao ,&nbsp;Zihong Yang ,&nbsp;Huaiqing Zhao ,&nbsp;Jie Shen ,&nbsp;Wenju Chang ,&nbsp;Zhiwei Liu ,&nbsp;Huaqiang Zeng","doi":"10.1039/d4qo02231a","DOIUrl":"10.1039/d4qo02231a","url":null,"abstract":"<div><div>H-bonded helically folded aromatic foldamers rely on the precise formation of H-bonds between each helicity codon and its neighboring codons to maintain their structure. We report here for the first time that the phenyl group, referred to as a non-helicity codon due to its inability to form H-bonds, does not necessarily disrupt the helical structure. Specifically, we modified our recently reported pyridine-based aquapentamers by sequentially replacing each of the five pyridine residues with a phenyl group, creating a series of five hybrid pentamers. The phenyl groups, unable to form H-bonds with the adjacent N–H bonds of the amides, introduce H-bond defects along the helical backbone. Despite these defects, three out of five pentamers still adopt a helical structure and function as highly selective and ultra-fast abiotic water channels, with the most efficient channel achieving a water transport rate of 1.8 × 10<sup>9</sup> H<sub>2</sub>O s<sup>−1</sup> per channel—approximately 30% of aquaporin Z's capacity.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1603-1611"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142936511","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
Correction: AI molecular catalysis: where are we now?
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-01
Zhenzhi Tan , Qi Yang , Sanzhong Luo
{"title":"Correction: AI molecular catalysis: where are we now?","authors":"Zhenzhi Tan ,&nbsp;Qi Yang ,&nbsp;Sanzhong Luo","doi":"","DOIUrl":"","url":null,"abstract":"<div><div>Correction for ‘AI molecular catalysis: where are we now?’ by Zhenzhi Tan <em>et al.</em>, <em>Org. Chem. Front.</em>, 2025, <span>https://doi.org/10.1039/d4qo02363c</span>.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Page 2131"},"PeriodicalIF":0.0,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143637232","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
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
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