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Chiral Brønsted acid-catalyzed intermolecular hydrophenoxylation of ynamides with biaryl phenols via sequential desymmetrization/kinetic resolution. 手性Brønsted酸催化双芳基苯酚与酰胺的分子间氢苯氧基化反应
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-13 DOI: 10.1039/d5ob00503e
Yu Yu, Min Chen
{"title":"Chiral Brønsted acid-catalyzed intermolecular hydrophenoxylation of ynamides with biaryl phenols <i>via</i> sequential desymmetrization/kinetic resolution.","authors":"Yu Yu, Min Chen","doi":"10.1039/d5ob00503e","DOIUrl":"https://doi.org/10.1039/d5ob00503e","url":null,"abstract":"<p><p>Herein we disclose the first catalytic asymmetric intermolecular hydrophenoxylation of ynamides with biaryl phenols under chiral Brønsted acid catalysis, providing axially chiral phenols. This enantioselective reaction proceeds through a sequential desymmetrizaiton/kinetic resolution process, which features mild reaction conditions and represents a rare paradigm of an organocatalytic asymmetric intermolecular reaction of ynamides.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143952200","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Mechanistic insights into photocatalytic nitrene transfer reactions of benzoyl azide in the presence of phosphoric acid. 磷酸存在下苯甲酰叠氮化物光催化亚硝基转移反应的机理研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-13 DOI: 10.1039/d5ob00538h
Jiaxin Lin, Hongmin Li, Xiaoguang Bao
{"title":"Mechanistic insights into photocatalytic nitrene transfer reactions of benzoyl azide in the presence of phosphoric acid.","authors":"Jiaxin Lin, Hongmin Li, Xiaoguang Bao","doi":"10.1039/d5ob00538h","DOIUrl":"https://doi.org/10.1039/d5ob00538h","url":null,"abstract":"<p><p>Computational studies were carried out to shed light on the mechanism of photocatalytic nitrene transfer reactions of benzoyl azide in the presence of phosphoric acid. The formed H-bonding complex of benzoyl azide with H<sub>3</sub>PO<sub>4</sub> would readily undergo single electron reduction with the excited *Ru(II) photocatalyst, followed by sequential proton transfer and N<sub>2</sub> dissociation to give a key N-centered radical. The energy transfer mechanistic pathway leading to a protonated nitrenium species, however, might not be feasible. The formed N-radical underwent different types of reactions with <i>N</i>-methylpyrrole and alkene, respectively, which was also rationalized.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143953003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Divergent synthetic studies towards bisabosqual A and fargenone B via an intramolecular SN2 reaction. 通过分子内SN2反应合成双角鲨A和法根酮B的不同研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-12 DOI: 10.1039/d5ob00655d
Chen Guo, Mao-Mei Zhu, Si-Ji Ze Lang, Ya-Wen Wang, Jian Xiao, Yu Peng
{"title":"Divergent synthetic studies towards bisabosqual A and fargenone B <i>via</i> an intramolecular S<sub>N</sub>2 reaction.","authors":"Chen Guo, Mao-Mei Zhu, Si-Ji Ze Lang, Ya-Wen Wang, Jian Xiao, Yu Peng","doi":"10.1039/d5ob00655d","DOIUrl":"https://doi.org/10.1039/d5ob00655d","url":null,"abstract":"<p><p>A divergent approach has been developed towards the synthetic studies of bisabosqual A and fargenone B for the first time. The key oxygenated five- or seven-membered ring in [6-5-6] and [6-7-6] tricyclic cores of these two natural products could be constructed through a regioselective intramolecular S<sub>N</sub>2 reaction from the common advanced intermediate 11.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143956152","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chromium(II)-catalyzed defluorinative reductive cross-coupling of acetals with α-trifluoromethyl alkenes. 铬（II）催化缩醛与α-三氟甲基烯烃的脱氟还原交偶联。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-12 DOI: 10.1039/d5ob00547g
Zaiyang Li, Meiming Luo, Xiaoming Zeng
{"title":"Chromium(II)-catalyzed defluorinative reductive cross-coupling of acetals with α-trifluoromethyl alkenes.","authors":"Zaiyang Li, Meiming Luo, Xiaoming Zeng","doi":"10.1039/d5ob00547g","DOIUrl":"https://doi.org/10.1039/d5ob00547g","url":null,"abstract":"<p><p>We report here the chromium(II)-catalyzed defluorinative reductive cross-coupling reaction of acetals with α-trifluoromethyl alkenes. α-Alkoxyalkyl radicals are generated from acetals under the synergistic effect of catalytic chromium and trimethylsilyl chloride. Subsequent selective cross-coupling of the radicals with α-trifluoromethyl alkenes provides a synthetic route to <i>gem</i>-difluoroalkenes that contain an alkoxy substituent at the homoallylic position.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143950827","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","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 iodosulfonylation of alkynes to access (E)-β-iodovinyl sulfones in water. 烷基的无金属碘磺酰化以获得水中的(E)-β-碘乙烯基砜。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-12 DOI: 10.1039/d5ob00483g
Guiting Peng, Fang Wei, Jiang Bai, Haixin Ding, Xin Yu, Qiang Xiao
{"title":"Metal-free iodosulfonylation of alkynes to access (<i>E</i>)-β-iodovinyl sulfones in water.","authors":"Guiting Peng, Fang Wei, Jiang Bai, Haixin Ding, Xin Yu, Qiang Xiao","doi":"10.1039/d5ob00483g","DOIUrl":"https://doi.org/10.1039/d5ob00483g","url":null,"abstract":"<p><p>With the escalating concerns regarding environmental pollution caused by organic solvents, chemists are increasingly focusing on conducting organic reactions in water, nature's chosen solvent for chemical synthesis. Herein, the development of metal-free iodosulfonylation of alkynes with <i>p</i>-toluenesulfonyl cyanide and NIS for the synthesis of (<i>E</i>)-β-iodovinyl sulfones in water is reported. This reaction gives the desired products in good to excellent yields with high regio- and stereoselectivity by using water as a green solvent at room temperature. This reaction could be readily scaled up, and synthetic application was also studied.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951631","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Direct C-H fluorination/heteroarylation of oxindoles with quinoxalin-2(1H)-ones using Selectfluor. 用selectflut直接C-H氟化/氧吲哚与喹诺沙林-2(1H)- 1的异芳基化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-12 DOI: 10.1039/d5ob00427f
Hui Qin, Guo-Liang Wei, Wen-Geng Xie, Xiao-Hong Mao, Fu-Wei Wang, Mei-Hua Bao, Xiao-Wei Zheng, Yi-Wen Zhang, Ping Huang
{"title":"Direct C-H fluorination/heteroarylation of oxindoles with quinoxalin-2(1<i>H</i>)-ones using Selectfluor.","authors":"Hui Qin, Guo-Liang Wei, Wen-Geng Xie, Xiao-Hong Mao, Fu-Wei Wang, Mei-Hua Bao, Xiao-Wei Zheng, Yi-Wen Zhang, Ping Huang","doi":"10.1039/d5ob00427f","DOIUrl":"https://doi.org/10.1039/d5ob00427f","url":null,"abstract":"<p><p>Herein, we present an efficient and feasible strategy for direct C-H fluorination and heteroarylation of oxindoles on the C-3 position having a C(sp<sup>3</sup>)-H bond with quinoxalin-2(1<i>H</i>)-ones based on a radical coupling reaction <i>via</i> Selectfluor, a bifunctional reagent, as both the oxidant and fluorine source. This methodology provides a potential protocol to obtain 3-heteroaryl 3-fluorooxindoles in medium to excellent yields.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955114","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Viscosity effects on the chemiluminescence emission of 1,2-dioxetanes in water. 粘度对1,2-二氧乙烷在水中化学发光的影响。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-09 DOI: 10.1039/d5ob00254k
Maidileyvis Castro Cabello, Palanisamy Kandhan, Peng Tao, Alexander R Lippert
{"title":"Viscosity effects on the chemiluminescence emission of 1,2-dioxetanes in water.","authors":"Maidileyvis Castro Cabello, Palanisamy Kandhan, Peng Tao, Alexander R Lippert","doi":"10.1039/d5ob00254k","DOIUrl":"https://doi.org/10.1039/d5ob00254k","url":null,"abstract":"<p><p>Chemiluminescence emission from 1,2-dioxetanes offers a versatile framework for molecular imaging in cells and animals. Here, we observe an increase in chemiluminescence emission intensity with increasing solvent viscosity in aqueous systems, and interpret these observations within the context of chemically initiated electron exchange luminescence (CIEEL), concerted charge transfer induced luminescence (CTIL), and gradually reversible charge transfer induced luminescence (GR-CTIL) mechanisms.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951280","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Squaramide-catalyzed aza-Michael/Michael cyclization cascade reaction: one-pot enantioselective construction of highly functionalized γ-lactams. 角鲨酰胺催化的aza-Michael/Michael环化级联反应：高功能化γ-内酰胺的单锅对映选择性构建。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-09 DOI: 10.1039/d5ob00572h
Sheng-Feng Wu, Zhi-Yuan Wang, Xing-Wen Sun
{"title":"Squaramide-catalyzed aza-Michael/Michael cyclization cascade reaction: one-pot enantioselective construction of highly functionalized γ-lactams.","authors":"Sheng-Feng Wu, Zhi-Yuan Wang, Xing-Wen Sun","doi":"10.1039/d5ob00572h","DOIUrl":"https://doi.org/10.1039/d5ob00572h","url":null,"abstract":"<p><p>We report a squaramide-catalyzed aza-Michael/Michael cyclization of nitroalkenes with 3-benzoylacylamides, facilitating the asymmetric synthesis of γ-lactams. This method efficiently generates a range of optically pure γ-lactams, in yields ranging from 25% to 90% and enantioselectivities 71% to 99% under mild conditions. Moreover, this reaction demonstrates exceptional compatibility with a variety of functional groups and offers a wide array of subsequent transformation possibilities.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955120","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Organocatalytic asymmetric synthesis of axially and centrally chiral heterotriarylmethanes by a Friedel-Crafts reaction. 用Friedel-Crafts反应有机催化不对称合成轴手性和中心手性杂三芳基甲烷。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-08 DOI: 10.1039/d5ob00532a
Yang Min, Hanxiao Shen, Shaoying Huang, Haorui Gu, Xufeng Lin
{"title":"Organocatalytic asymmetric synthesis of axially and centrally chiral heterotriarylmethanes by a Friedel-Crafts reaction.","authors":"Yang Min, Hanxiao Shen, Shaoying Huang, Haorui Gu, Xufeng Lin","doi":"10.1039/d5ob00532a","DOIUrl":"https://doi.org/10.1039/d5ob00532a","url":null,"abstract":"<p><p>A highly enantioselective Friedel-Crafts reaction between C2-unsubstituted naphthyl-indoles and racemic 3-methylated-3<i>H</i>-pyrrolides catalyzed by chiral phosphoric acids has been developed. This reaction provides an efficient and facile route to a series of heterotricyclic triarylmethanes containing axially chiral naphthyl-indole and centrally chiral pyrrole moieties under mild conditions. Moreover, biological evaluation discovered one of these products with promising antitumor activity, and demonstrates its potential application in medicinal chemistry.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143958723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
One-pot green synthesis of N-acetylglycine from renewable N-acetyl glucosamine† 可再生n -乙酰氨基葡萄糖一锅绿色合成n -乙酰氨基甘氨酸。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-07 DOI: 10.1039/D5OB00577A
Qingya Cao, Jinhang Dai, Ziting Du, Gang Chen, Fukun Li, Ting Qi, Ruiqi Wang, Weilu Wang, Jun Zhao and Chenxi Huang
{"title":"One-pot green synthesis of N-acetylglycine from renewable N-acetyl glucosamine†","authors":"Qingya Cao, Jinhang Dai, Ziting Du, Gang Chen, Fukun Li, Ting Qi, Ruiqi Wang, Weilu Wang, Jun Zhao and Chenxi Huang","doi":"10.1039/D5OB00577A","DOIUrl":"10.1039/D5OB00577A","url":null,"abstract":"<p >One-pot synthesis of <em>N</em>-acetylglycine from <em>N</em>-acetyl glucosamine using a combination of heterogeneous MgO and Ag<small><sub>2</sub></small>O was demonstrated, achieving an enhanced yield of 29% in water under mild conditions. Compared to traditional methods, environment unfriendly Strecker reactions are avoided. Experimental and DFT results revealed that 2-acetamido acetaldehyde was identified as the main intermediate. This work provides an example for self-nitrogen supplied synthesis of valuable organonitrogen compounds from chitin biomass.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5126-5132"},"PeriodicalIF":2.9,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143957336","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","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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