A visible-light-driven, transition-metal-free dehalogenative oximation of simple alkyl halides has been developed, exploiting a boryl radical-mediated halogen atom transfer (XAT) process. This strategy efficiently converts readily available alkyl halides into diverse oximes under mild conditions. Gram-scale synthesis, diverse derivatization of the oxime products, and a concise route to Tioxazafen collectively highlight the strategy’s broad synthetic utility. The Z/E selectivity in the synthesis of aryl oximes can be controlled by the addition or omission of a triplet photosensitizer. Therefore, this protocol offers a practical paradigm for the diversified transformation of simple alkyl halides under transition metal-free conditions.
{"title":"Visible-light-driven dehalogenative oximation of alkyl halides","authors":"Feng Xu, Dayong Shi, Ruihua Liu","doi":"10.1039/d6qo00020g","DOIUrl":"https://doi.org/10.1039/d6qo00020g","url":null,"abstract":"A visible-light-driven, transition-metal-free dehalogenative oximation of simple alkyl halides has been developed, exploiting a boryl radical-mediated halogen atom transfer (XAT) process. This strategy efficiently converts readily available alkyl halides into diverse oximes under mild conditions. Gram-scale synthesis, diverse derivatization of the oxime products, and a concise route to Tioxazafen collectively highlight the strategy’s broad synthetic utility. The Z/E selectivity in the synthesis of aryl oximes can be controlled by the addition or omission of a triplet photosensitizer. Therefore, this protocol offers a practical paradigm for the diversified transformation of simple alkyl halides under transition metal-free conditions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"85 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147489538","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Herein, we report a photocatalytic three-component radical coupling that enables the dual functionalization of alkenes with monofluoroalkenyl and sulfonyl/phosphonyl groups. This strategy offers a streamlined access to (E)-β-fluoroalkenyl sulfones and phosphonates in good yields and with high stereoselectivity from aryl gem-difluoroalkenes, various alkenes, and sodium sulfinates or diphenylphosphine oxide under mild conditions. The method is robust, exhibiting wide functional group tolerance and broad substrate scope. Furthermore, gram-scale reactions and subsequent derivatizations proceed smoothly, underscoring the practicality and scalability of our methodology
{"title":"Stereoselective synthesis of β-sulfonyl and β-phosphonyl (E)-fluoroalkenes via visible-light-induced multicomponent defluorinative coupling","authors":"Liping Wu, Kangjie Fan, Jiamei Ni, Jialuo Ying, Chaojie Wang, Zhiwei Chen","doi":"10.1039/d6qo00208k","DOIUrl":"https://doi.org/10.1039/d6qo00208k","url":null,"abstract":"Herein, we report a photocatalytic three-component radical coupling that enables the dual functionalization of alkenes with monofluoroalkenyl and sulfonyl/phosphonyl groups. This strategy offers a streamlined access to (<em>E</em>)-β-fluoroalkenyl sulfones and phosphonates in good yields and with high stereoselectivity from aryl <em>gem</em>-difluoroalkenes, various alkenes, and sodium sulfinates or diphenylphosphine oxide under mild conditions. The method is robust, exhibiting wide functional group tolerance and broad substrate scope. Furthermore, gram-scale reactions and subsequent derivatizations proceed smoothly, underscoring the practicality and scalability of our methodology","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"146 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147492508","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Here we report a new homoleptic Ir(NHC) photocatalyst, mer-Ir(pmp)3 which is the first Ir(C^C)3 photocatalyst to operate effectively using excitation sources peaking in the visible (λ exc = 427, 440 and 456 nm). In line with previously reported Ir(C^C)3 photocatalysts, mer-Ir(pmp)3 is a potent photoreductant, reducing substrates up to Ered = -2.7 V vs. SCE and energy transfer catalyst, sensitizing substrates up to ET = 3.00 eV. Furthermore, mer-Ir(pmp)3 can engage in dual nickel photoredox catalysis on account of its red-shifted absorption spectrum and anodically shifted redox potentials. Compared to the literature-known photocatalysts, [Ir(dF(CF3)ppy)2(dtbbpy)]PF6, 4CzIPN and [Ru(bpy)3](PF6)2, mer-Ir(pmp)3 achieves competitive or improved yields for the amination of aryl bromides and exhibits good photostability across a range of different conditions.
{"title":"mer-Ir(pmp)3 as a strongly photoreducing and stable Ir(C^C)3 photocatalyst for metallaphotoredox catalysis","authors":"Máire Griffin, Eli Zysman-Colman","doi":"10.1039/d6qo00086j","DOIUrl":"https://doi.org/10.1039/d6qo00086j","url":null,"abstract":"Here we report a new homoleptic Ir(NHC) photocatalyst, mer-Ir(pmp)3 which is the first Ir(C^C)3 photocatalyst to operate effectively using excitation sources peaking in the visible (λ exc = 427, 440 and 456 nm). In line with previously reported Ir(C^C)3 photocatalysts, mer-Ir(pmp)3 is a potent photoreductant, reducing substrates up to Ered = -2.7 V vs. SCE and energy transfer catalyst, sensitizing substrates up to ET = 3.00 eV. Furthermore, mer-Ir(pmp)3 can engage in dual nickel photoredox catalysis on account of its red-shifted absorption spectrum and anodically shifted redox potentials. Compared to the literature-known photocatalysts, [Ir(dF(CF3)ppy)2(dtbbpy)]PF6, 4CzIPN and [Ru(bpy)3](PF6)2, mer-Ir(pmp)3 achieves competitive or improved yields for the amination of aryl bromides and exhibits good photostability across a range of different conditions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147489539","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A novel method for constructing 3-(2-allyl)-indolyl substituted gem-difluoroalkenes that relies on Sc(OTf)3-catalyzed C2selective allylation/defluorination cascade of trifluoromethylated 3-indolylmethanols has been realized. This diazo-free protocol features exclusive regioselectivity and broad substrate scope. In addition, the application of this protocol has been demonstrated by the one-step transformation of the obtained gem-difluoroalkenes into valuable and functionalized 3amino-carbazole skeletons through DBN-promoted defluorinative annulation under catalyst-free conditions.
{"title":"Access to 3-Amino-carbazoles from CF3-3-Indolylmethanols via Sc(OTf)3-Catalyzed C2-Defluorinative Allylation and DBN-Promoted Dedluorinative Annulation","authors":"Qing Liu, Xin Liu, Weidong Rao","doi":"10.1039/d6qo00163g","DOIUrl":"https://doi.org/10.1039/d6qo00163g","url":null,"abstract":"A novel method for constructing 3-(2-allyl)-indolyl substituted gem-difluoroalkenes that relies on Sc(OTf)3-catalyzed C2selective allylation/defluorination cascade of trifluoromethylated 3-indolylmethanols has been realized. This diazo-free protocol features exclusive regioselectivity and broad substrate scope. In addition, the application of this protocol has been demonstrated by the one-step transformation of the obtained gem-difluoroalkenes into valuable and functionalized 3amino-carbazole skeletons through DBN-promoted defluorinative annulation under catalyst-free conditions.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147489540","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Miguel Angel Valle-Amores, Benedetta Carli, Ian MacLean, Lara Martínez-Fernández, Raúl Pérez-Ruiz, Leyre Marzo, Alberto Fraile, Jose Aleman
Expanding the toolbox of C-H functionalization reactions applicable to the late-stage modification of complex molecules of interest in medicinal chemistry is a key strategy for drug development. Herein, we report an unusual visible-light-induced olefinic C(sp 2 )-H functionalization of olefins with diazo derivatives by means of an Ir(III) photocatalyst. The approach demonstrates the potential for targeting double bonds such as those present in enol ethers and further studied in 1,1disubstituted alkenes. This efficient methodology affords unprecedented Heck-type products from good to excellent yields using mild conditions. Further derivatizations of final products are shown to demonstrate the robustness of the methodology. The reaction pathway was validated by electrochemical and photophysical experiments as well as computational studies.
{"title":"Visible-Light-Driven C-H Functionalization of Double Bonds with Diazo Compounds under Mild Reaction Conditions","authors":"Miguel Angel Valle-Amores, Benedetta Carli, Ian MacLean, Lara Martínez-Fernández, Raúl Pérez-Ruiz, Leyre Marzo, Alberto Fraile, Jose Aleman","doi":"10.1039/d5qo01537e","DOIUrl":"https://doi.org/10.1039/d5qo01537e","url":null,"abstract":"Expanding the toolbox of C-H functionalization reactions applicable to the late-stage modification of complex molecules of interest in medicinal chemistry is a key strategy for drug development. Herein, we report an unusual visible-light-induced olefinic C(sp 2 )-H functionalization of olefins with diazo derivatives by means of an Ir(III) photocatalyst. The approach demonstrates the potential for targeting double bonds such as those present in enol ethers and further studied in 1,1disubstituted alkenes. This efficient methodology affords unprecedented Heck-type products from good to excellent yields using mild conditions. Further derivatizations of final products are shown to demonstrate the robustness of the methodology. The reaction pathway was validated by electrochemical and photophysical experiments as well as computational studies.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"1 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147490162","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xia Liu, Zhi Li, Congman Song, Guiqing Xu, Duanyang Kong
Regioselective carboxylation of indoles using CO₂ remains a longstanding challenge, particularly for achieving controllable access to both N1-and C3-carboxylated products under unified conditions. Herein, we report a temperature-controlled, regiodivergent strategy for indole carboxylation enabled by cesium triphenylacetate as a benign CO₂-transfer reagent. This metal-free protocol allows selective N1-or C3-carboxylation from the same indole substrates simply by adjusting the reaction temperature and reagent loading, without external CO₂ pressure or strong bases. The method exhibits broad substrate scope, predictable regioselectivity, and good functional-group tolerance, and is readily applicable to near-stoichiometric 13 C isotope labeling. Mechanistic studies reveal that reversible N1carboxylation and temperature-dependent redistribution of a delocalized indolyl anion are responsible for the observed regioselectivity. This work establishes a unified and practical platform for regiodivergent indole carboxylation and introduces a distinct CO₂-transfer paradigm for regioselective C-H functionalization of heteroarenes. 2
{"title":"Regiodivergent N1-and C3-Carboxylation of Indoles","authors":"Xia Liu, Zhi Li, Congman Song, Guiqing Xu, Duanyang Kong","doi":"10.1039/d6qo00306k","DOIUrl":"https://doi.org/10.1039/d6qo00306k","url":null,"abstract":"Regioselective carboxylation of indoles using CO₂ remains a longstanding challenge, particularly for achieving controllable access to both N1-and C3-carboxylated products under unified conditions. Herein, we report a temperature-controlled, regiodivergent strategy for indole carboxylation enabled by cesium triphenylacetate as a benign CO₂-transfer reagent. This metal-free protocol allows selective N1-or C3-carboxylation from the same indole substrates simply by adjusting the reaction temperature and reagent loading, without external CO₂ pressure or strong bases. The method exhibits broad substrate scope, predictable regioselectivity, and good functional-group tolerance, and is readily applicable to near-stoichiometric 13 C isotope labeling. Mechanistic studies reveal that reversible N1carboxylation and temperature-dependent redistribution of a delocalized indolyl anion are responsible for the observed regioselectivity. This work establishes a unified and practical platform for regiodivergent indole carboxylation and introduces a distinct CO₂-transfer paradigm for regioselective C-H functionalization of heteroarenes. 2","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"28 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147478160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The investigation of molecular chirality within interlocked molecules is an appealing research area however, the synthesis of optically active interlocked molecules poses considerable challenges. In this study, we combined chiral spiroborate formation with the chiral recognition of secondary ammonium ions by a borate-containing crown macrocycle to synthesise optically active pseudo[2]rotaxanes from achiral bis-catechols, chiral amines and boric acid. We examined how the chiral centres in amines influence the stereoselectivity of pseudo[2]rotaxanes under kinetic and thermodynamic conditions. Because the reversible borate-forming reaction creates a dynamic covalent bond between B and O, it facilitates the stereoselective formation of optically active pseudo[2]rotaxanes, achieving a diastereoselectivity of up to 40:1. After isolating the pseudo[2]rotaxanes, X-ray crystallography, circular dichroism spectroscopy and density functional theory calculations were used to reveal their absolute configuration.
{"title":"Synthesis of chiral rotaxanes: Controlling the molecular chirality of bis-catechol spiroborate through threading","authors":"Kion Takada, Rin Usui, Takumi Takizawa, Masaya Naito, Yusuke Okada, Nagao Kobayashi, Shinobu Miyagawa, Yuji Tokunaga","doi":"10.1039/d5qo01744k","DOIUrl":"https://doi.org/10.1039/d5qo01744k","url":null,"abstract":"The investigation of molecular chirality within interlocked molecules is an appealing research area however, the synthesis of optically active interlocked molecules poses considerable challenges. In this study, we combined chiral spiroborate formation with the chiral recognition of secondary ammonium ions by a borate-containing crown macrocycle to synthesise optically active pseudo[2]rotaxanes from achiral bis-catechols, chiral amines and boric acid. We examined how the chiral centres in amines influence the stereoselectivity of pseudo[2]rotaxanes under kinetic and thermodynamic conditions. Because the reversible borate-forming reaction creates a dynamic covalent bond between B and O, it facilitates the stereoselective formation of optically active pseudo[2]rotaxanes, achieving a diastereoselectivity of up to 40:1. After isolating the pseudo[2]rotaxanes, X-ray crystallography, circular dichroism spectroscopy and density functional theory calculations were used to reveal their absolute configuration.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"120 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147489541","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Expression of concern for ‘Dithiocarbamate-mediated thioamidation of arylglyoxylic acids by decarboxylative–decarbonylative C–C bond formation reactions’ by Debabrata Patra et al., Org. Chem. Front., 2023, 10, 1686–1693, https://doi.org/10.1039/D3QO00032J.
{"title":"Expression of concern: Dithiocarbamate-mediated thioamidation of arylglyoxylic acids by decarboxylative–decarbonylative C–C bond formation reactions","authors":"Debabrata Patra, Amit Saha","doi":"10.1039/d6qo90015a","DOIUrl":"https://doi.org/10.1039/d6qo90015a","url":null,"abstract":"Expression of concern for ‘Dithiocarbamate-mediated thioamidation of arylglyoxylic acids by decarboxylative–decarbonylative C–C bond formation reactions’ by Debabrata Patra <em>et al.</em>, <em>Org. Chem. Front.</em>, 2023, <strong>10</strong>, 1686–1693, https://doi.org/10.1039/D3QO00032J.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"96 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147478188","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Francesco Riina, Giulio Chiarello, Lorenzo Poletti, Daniele Ragno, Carmela De Risi, Mirco Natali, Federico Droghetti, Alessandro Massi, Graziano Di Carmine
Two visible-light-mediated, catalyst-free strategies for the synthesis of α-C-glycoside conjugates are reported. The methods exploit electron donor–acceptor (EDA) complex activation and in situ generated photocatalytically active species to trigger Giese-like radical additions from glycosyl iodide to electron-poor olefins under mild conditions. Iodide derived glycosyl donors participate, enabling the formation of C-glycosidic linkages across a broad range of mono- and disaccharide substrates, dehydroalanine derivatives, and bisphosphonate acceptors. Mechanistic studies indicate that distinct activation pathways operate depending on the reaction conditions: deprotonated Hantzsch ester–halogen EDA complexes in the presence of base, and autocatalytic photoredox processes involving transient streptocyanine-type dyes generated from tertiary amines under irradiation. These findings demonstrate that selective C–C bond formation at the anomeric position can be achieved without exogenous photocatalysts, while highlighting the non-innocent role of amines in visible light driven radical transformations.
报道了两种可见光介导、无催化剂的α- c -糖苷偶联物合成策略。该方法利用电子供体-受体（EDA）复合物活化和原位生成光催化活性物质，在温和条件下触发碘化糖基向缺电子烯烃的giese类自由基加成。碘衍生的糖基供体参与，使c -糖苷键在广泛的单糖和双糖底物、脱氢丙氨酸衍生物和双膦酸盐受体之间形成。机理研究表明，不同的激活途径取决于反应条件：在碱存在下脱质子的Hantzsch酯-卤素EDA复合物，以及在辐照下由叔胺生成的瞬态链菁型染料的自催化光氧化还原过程。这些发现表明，在没有外源光催化剂的情况下，可以在端粒位置形成选择性的C-C键，同时突出了胺在可见光驱动的自由基转化中的非无害作用。
{"title":"Synthesis of α-C-Glycoside Conjugates via Giese-like Reaction Triggered by Photoactivated Electron Donor–Acceptor (EDA) Complexes and in situ photocatalytic species","authors":"Francesco Riina, Giulio Chiarello, Lorenzo Poletti, Daniele Ragno, Carmela De Risi, Mirco Natali, Federico Droghetti, Alessandro Massi, Graziano Di Carmine","doi":"10.1039/d6qo00174b","DOIUrl":"https://doi.org/10.1039/d6qo00174b","url":null,"abstract":"Two visible-light-mediated, catalyst-free strategies for the synthesis of α-C-glycoside conjugates are reported. The methods exploit electron donor–acceptor (EDA) complex activation and in situ generated photocatalytically active species to trigger Giese-like radical additions from glycosyl iodide to electron-poor olefins under mild conditions. Iodide derived glycosyl donors participate, enabling the formation of C-glycosidic linkages across a broad range of mono- and disaccharide substrates, dehydroalanine derivatives, and bisphosphonate acceptors. Mechanistic studies indicate that distinct activation pathways operate depending on the reaction conditions: deprotonated Hantzsch ester–halogen EDA complexes in the presence of base, and autocatalytic photoredox processes involving transient streptocyanine-type dyes generated from tertiary amines under irradiation. These findings demonstrate that selective C–C bond formation at the anomeric position can be achieved without exogenous photocatalysts, while highlighting the non-innocent role of amines in visible light driven radical transformations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"6 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147478189","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The reported thioamidation reaction of phenylglyoxylic acid, PhCOCO2H, gives only a 5% yield of thioamide product, and not the 96% yield reported in Org. Chem. Front., 2023, 10, 1686. The proposed Pd(II) catalyst plays no role in the reaction. Labelled phenylglyoxylic acid, Ph13COCO2H, gave a thioamide product where the 13C label is retained. This rules out the suggested mechanism, which involves a phenyl radical derived from decarbonylation of benzoyl radical.
{"title":"Comment on “Dithiocarbamate-mediated thioamidation of arylglyoxylic acids by decarboxylative–decarbonylative C–C bond formation reactions” by D. Patra and A. Saha, Org. Chem. Front., 2023, 10, 1686","authors":"Xavier Creary","doi":"10.1039/d4qo00393d","DOIUrl":"https://doi.org/10.1039/d4qo00393d","url":null,"abstract":"The reported thioamidation reaction of phenylglyoxylic acid, PhCOCO<small><sub>2</sub></small>H, gives only a 5% yield of thioamide product, and not the 96% yield reported in <em>Org. Chem. Front.</em>, 2023, <strong>10</strong>, 1686. The proposed Pd(<small>II</small>) catalyst plays no role in the reaction. Labelled phenylglyoxylic acid, Ph<small><sup>13</sup></small>COCO<small><sub>2</sub></small>H, gave a thioamide product where the <small><sup>13</sup></small>C label is retained. This rules out the suggested mechanism, which involves a phenyl radical derived from decarbonylation of benzoyl radical.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"35 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147466146","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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