We report a novel metal-free method for selectively reducing aromatic alkynes and alkenes by using phosphonic acid. When combined with molecular iodine, this system reduces aromatic alkynes to the corresponding (E)-alkenes and alkanes in high yields. Additionally, various aromatic alkenes can be directly reduced with comparable efficiency. This protocol features low cost, simple conditions, and the avoidance of metal catalysts.
{"title":"Metal-Free Selective Reduction of Aromatic Alkynes and Alkenes Using Phosphonic Acid","authors":"Mengfan Wang,Yuxiang Xie,Shiqi Ou,Zhicheng Jia,Xiaoxiang Xi,Li-Biao Han,Jing Xiao","doi":"10.1021/acs.joc.5c02921","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02921","url":null,"abstract":"We report a novel metal-free method for selectively reducing aromatic alkynes and alkenes by using phosphonic acid. When combined with molecular iodine, this system reduces aromatic alkynes to the corresponding (E)-alkenes and alkanes in high yields. Additionally, various aromatic alkenes can be directly reduced with comparable efficiency. This protocol features low cost, simple conditions, and the avoidance of metal catalysts.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"80 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098104","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alex Boateng,Isai Ramakrishna,Tomohiro Hattori,Hisashi Yamamoto
Although the conventional approach to peptide synthesis has been employed for decades, it requires multiple protection–deprotection steps, stoichiometric amounts of coupling reagents and additives, and large volumes of solvent. Consequently, it is accompanied by limitations, such as low atom economy and waste generation. One favorable alternative to combating this problem is the direct formation of peptide bonds using unprotected amino acids. However, this strategy poses issues, such as the low solubility of the unprotected amino acids in organic solvents, unwanted side reactions, and racemization. To overcome these drawbacks, a method has been developed for direct peptide bond formation using trimethoxysilane, an inexpensive and commercially available reagent. Trimethoxysilane helps solubilize the unprotected amino acids in organic solvents, transiently protects the amine group, and simultaneously activates carboxylic acids for coupling. This method represents a one-pot strategy for the synthesis of N-terminal free dipeptides from unprotected amino acids and amino acid tert-butyl esters at 70 °C for 20 h in moderate to good yields (up to 95% yields). Notably, the reactions exhibit high stereoselectivities of >20:1 dr with broad substrate scope compatibility, and the developed approach was applied in the synthesis of tripeptides including bioactive motifs.
{"title":"Trimethoxysilane-Mediated Peptide Bond Formation from Unprotected Amino Acids and Amino Acid t-Butyl Esters","authors":"Alex Boateng,Isai Ramakrishna,Tomohiro Hattori,Hisashi Yamamoto","doi":"10.1021/acs.joc.5c02942","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02942","url":null,"abstract":"Although the conventional approach to peptide synthesis has been employed for decades, it requires multiple protection–deprotection steps, stoichiometric amounts of coupling reagents and additives, and large volumes of solvent. Consequently, it is accompanied by limitations, such as low atom economy and waste generation. One favorable alternative to combating this problem is the direct formation of peptide bonds using unprotected amino acids. However, this strategy poses issues, such as the low solubility of the unprotected amino acids in organic solvents, unwanted side reactions, and racemization. To overcome these drawbacks, a method has been developed for direct peptide bond formation using trimethoxysilane, an inexpensive and commercially available reagent. Trimethoxysilane helps solubilize the unprotected amino acids in organic solvents, transiently protects the amine group, and simultaneously activates carboxylic acids for coupling. This method represents a one-pot strategy for the synthesis of N-terminal free dipeptides from unprotected amino acids and amino acid tert-butyl esters at 70 °C for 20 h in moderate to good yields (up to 95% yields). Notably, the reactions exhibit high stereoselectivities of >20:1 dr with broad substrate scope compatibility, and the developed approach was applied in the synthesis of tripeptides including bioactive motifs.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"67 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098107","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Siao Lu,Minghan Li,Jingyi Zhang,Linyu Zheng,Zixun Gao,Bintao Liu,Rongfeng Huang,Yulin Feng,Fangling Lu
The structural modification of drug molecules is a fundamental approach to optimizing lead compounds designed to achieve concurrent improvements in efficacy, pharmacokinetics, and safety. Herein, we disclose an efficient and eco-benign electrochemical oxidative protocol for regioselective and chemoselective difunctionalization of the sulindac alkene scaffold under transition-metal-free, exogenous oxidant-free, and base-free conditions. This methodology delivers diverse sulindac derivatives in moderate to excellent yields (up to 92%) with a broad functional group tolerance. Mechanistic studies reveal a radical–radical cross-coupling process, offering a novel strategy for alkene difunctionalization.
{"title":"Electrochemical Oxidation-Induced Difunctionalization of the Sulindac Alkene Moiety with Diselenides","authors":"Siao Lu,Minghan Li,Jingyi Zhang,Linyu Zheng,Zixun Gao,Bintao Liu,Rongfeng Huang,Yulin Feng,Fangling Lu","doi":"10.1021/acs.joc.5c02865","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02865","url":null,"abstract":"The structural modification of drug molecules is a fundamental approach to optimizing lead compounds designed to achieve concurrent improvements in efficacy, pharmacokinetics, and safety. Herein, we disclose an efficient and eco-benign electrochemical oxidative protocol for regioselective and chemoselective difunctionalization of the sulindac alkene scaffold under transition-metal-free, exogenous oxidant-free, and base-free conditions. This methodology delivers diverse sulindac derivatives in moderate to excellent yields (up to 92%) with a broad functional group tolerance. Mechanistic studies reveal a radical–radical cross-coupling process, offering a novel strategy for alkene difunctionalization.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098112","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A simple pseudofour-component reaction catalyzed by CuBr2 has been developed to deliver C3-imidazoylquinoxalinones with decent yields from quinoxalin-2(1H)-ones, acetophenones, and ammonium persulfate in DMSO. This process follows a sequence of cross-dehydrogenative coupling/Kornblum oxidation/aza-cyclization, creating selectively four new C–C, two C–N, and C═N bonds. Interestingly, the Kornblum oxidation step can be skipped by simply replacing CuBr2 with Cu(OAc)2. This alteration leads to high-value C3-pyridylquinoxalinones. Notably, DMSO serves both as a C–H source for pyridine ring synthesis and an effective solvent for this conversion. In addition, the acquired 3-imidazolyl- and pyridylquinoxalinones were transmuted into value-added 3-(imidazo[1,2-a]pyrazin-3-yl)quinoxalinone and 2-sulfonylquinoxalines, showcasing the synthetic utility of our method.
{"title":"Switching Copper(II)-Catalytic Process for the Selective Access to C3-Imidazolyl- and Pyridylquinoxalin-2(1H)-ones","authors":"S Banuprakash Goud,Raju L. Dhakar,Sampak Samanta","doi":"10.1021/acs.joc.5c03006","DOIUrl":"https://doi.org/10.1021/acs.joc.5c03006","url":null,"abstract":"A simple pseudofour-component reaction catalyzed by CuBr2 has been developed to deliver C3-imidazoylquinoxalinones with decent yields from quinoxalin-2(1H)-ones, acetophenones, and ammonium persulfate in DMSO. This process follows a sequence of cross-dehydrogenative coupling/Kornblum oxidation/aza-cyclization, creating selectively four new C–C, two C–N, and C═N bonds. Interestingly, the Kornblum oxidation step can be skipped by simply replacing CuBr2 with Cu(OAc)2. This alteration leads to high-value C3-pyridylquinoxalinones. Notably, DMSO serves both as a C–H source for pyridine ring synthesis and an effective solvent for this conversion. In addition, the acquired 3-imidazolyl- and pyridylquinoxalinones were transmuted into value-added 3-(imidazo[1,2-a]pyrazin-3-yl)quinoxalinone and 2-sulfonylquinoxalines, showcasing the synthetic utility of our method.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"58 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098111","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We report a highly efficient protocol for the synthesis of silylated/germylated phenanthridine derivatives through the photocatalytic radical cascade cyclization of N-aryl acrylamides. A simple N-aminopyridinium salt was used as a hydrogen atom transfer reagent to generate a silyl/germyl radical under photoredox catalytic conditions. This method demonstrates a broad substrate scope and is suitable for the late-stage functionalization of natural products and pharmaceuticals with a shorter reaction time. Moreover, photophysical studies of selected phenanthridine derivatives highlight the promising luminescence properties with excellent fluorescence emission efficacy (quantum yields).
{"title":"Photocatalytic Silylation/Germylation and Cascade Cyclization of N-(o-Cyanobiaryl)acrylamides: Access to Silylated and Germylated Phenanthridines","authors":"Shivam Kumar Maurya, Sermadurai Selvakumar","doi":"10.1021/acs.joc.5c02890","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02890","url":null,"abstract":"We report a highly efficient protocol for the synthesis of silylated/germylated phenanthridine derivatives through the photocatalytic radical cascade cyclization of <i>N</i>-aryl acrylamides. A simple <i>N</i>-aminopyridinium salt was used as a hydrogen atom transfer reagent to generate a silyl/germyl radical under photoredox catalytic conditions. This method demonstrates a broad substrate scope and is suitable for the late-stage functionalization of natural products and pharmaceuticals with a shorter reaction time. Moreover, photophysical studies of selected phenanthridine derivatives highlight the promising luminescence properties with excellent fluorescence emission efficacy (quantum yields).","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"43 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146089771","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The fluorinated functional groups represent privileged and irreplaceable motifs in pharmaceuticals and agrochemicals. However, certain fluorinated group-containing compounds, including trifluoromethyl group have recently been classified as per- and polyfluoroalkyl substances (PFAS) due to their high stability, environmental mobility and toxicity. Fortunately, halodifluoromethyl groups (-CF2X, X = Cl, Br, I) can be degraded into nonpersistent compounds and serve as the halogen bond donors, which are distinctive among fluorinated substituents. Despite the importance of these groups, a general method for the installment of halodifluoromethyl groups into aromatics remains underexplored. Here we report a facile and efficient synthesis of chloro(bromo, iodo)difluoromethylarenes through nickel-mediated halodifluoromethylation of (hetero)aryl chlorides(bromides) with TMSCF2Cl or TMSCF2Br. The distinct reaction mechanism involves the insertion of difluorocarbene into the in situ generated aryl nickel(II) halide complex (Ar-Ni(II)-X), followed by oxidant-induced reductive elimination from the resulting aryldifluoromethyl nickel(II) intermediate (ArCF2-Ni(II)-X).
氟化官能团在药品和农用化学品中代表着特权和不可替代的基序。然而，某些含氟基团化合物，包括三氟甲基，由于其高稳定性、环境流动性和毒性，最近已被归类为单氟烷基物质和多氟烷基物质。幸运的是，卤代二氟甲基（-CF2X, X = Cl, Br， I）可以降解为非持久性化合物，并作为卤素键给体，这在氟化取代基中是独特的。尽管这些基团很重要，但在芳烃中安装卤二氟甲基的一般方法仍未得到充分探索。本文报道了用TMSCF2Cl或TMSCF2Br对（杂）芳基氯（溴）进行镍介导的卤代二氟甲基化反应，简便有效地合成了氯（溴，碘）二氟甲基芳烃。不同的反应机制包括将二氟化苯插入原位生成的芳基镍（II）卤化物配合物（Ar-Ni(II)-X）中，然后由氧化诱导的芳基二氟甲基镍（II）中间体（ArCF2-Ni(II)-X）的还原消除。
{"title":"Insertion of Difluorocarbene into Nickel Complexes to Access Chloro(Bromo, iodo)Difluoromethylarenes.","authors":"Xiang-Yi Chen,Jia-Yi Shou,Feng-Ling Qing","doi":"10.1021/acs.joc.5c02739","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02739","url":null,"abstract":"The fluorinated functional groups represent privileged and irreplaceable motifs in pharmaceuticals and agrochemicals. However, certain fluorinated group-containing compounds, including trifluoromethyl group have recently been classified as per- and polyfluoroalkyl substances (PFAS) due to their high stability, environmental mobility and toxicity. Fortunately, halodifluoromethyl groups (-CF2X, X = Cl, Br, I) can be degraded into nonpersistent compounds and serve as the halogen bond donors, which are distinctive among fluorinated substituents. Despite the importance of these groups, a general method for the installment of halodifluoromethyl groups into aromatics remains underexplored. Here we report a facile and efficient synthesis of chloro(bromo, iodo)difluoromethylarenes through nickel-mediated halodifluoromethylation of (hetero)aryl chlorides(bromides) with TMSCF2Cl or TMSCF2Br. The distinct reaction mechanism involves the insertion of difluorocarbene into the in situ generated aryl nickel(II) halide complex (Ar-Ni(II)-X), followed by oxidant-induced reductive elimination from the resulting aryldifluoromethyl nickel(II) intermediate (ArCF2-Ni(II)-X).","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146089160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alexander R Pelley,Salman Bagherzadeh,Jian-Bin Lin,Huck K Grover
A scalable synthesis of α,β-unsaturated diazoketones has been developed through the reaction of 1-iodoenones with N,N'-ditosylhydrazine. 1-Chloroenones, accessible from aldehydes via a Wittig-type homologation, undergo in situ halide exchange and diazo transfer in a one-pot sequence that minimizes purification and enhances efficiency. This strategy offers practical access to α,β-unsaturated diazoketones, which serve as versatile intermediates for synthesis and reaction discovery. In addition, selective formation of dihydropyridazinones through a 1,4-addition pathway is described.
{"title":"Synthesis of α,β-Unsaturated Diazoketones through the Use of N,N'-Ditosylhydrazine.","authors":"Alexander R Pelley,Salman Bagherzadeh,Jian-Bin Lin,Huck K Grover","doi":"10.1021/acs.joc.5c02682","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02682","url":null,"abstract":"A scalable synthesis of α,β-unsaturated diazoketones has been developed through the reaction of 1-iodoenones with N,N'-ditosylhydrazine. 1-Chloroenones, accessible from aldehydes via a Wittig-type homologation, undergo in situ halide exchange and diazo transfer in a one-pot sequence that minimizes purification and enhances efficiency. This strategy offers practical access to α,β-unsaturated diazoketones, which serve as versatile intermediates for synthesis and reaction discovery. In addition, selective formation of dihydropyridazinones through a 1,4-addition pathway is described.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"71 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146089188","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ankita Pradhan,Archana Chutia,Hunmoina Phukon,Anil K Saikia
A novel SnCl4-mediated one-pot, three-component methodology has been developed for the direct synthesis of a diverse array of 4-aminoquinoline derivatives utilizing 2-aminobenzonitriles, aldehydes, and active methylene compounds. The reaction proceeds smoothly via a series of tandem reactions, including condensation followed by intramolecular cyclization and aromatization, to afford highly substituted 4-aminoquinolines in good to excellent yields (up to 88%) within 12-14 h. The protocol exhibits a broad substrate scope and excellent functional group tolerance. Notably, the strategy can also be applied for the construction of highly fused polycyclic frameworks through C-H activation and annulation and allows for the efficient synthesis of diacylated derivatives, highlighting its broad synthetic utility.
{"title":"One-Pot, Three-Component Cascade Synthesis of 4-Amino Quinoline Derivatives from 2-Aminobenzonitriles, Aldehydes, and Active Methylene Compounds.","authors":"Ankita Pradhan,Archana Chutia,Hunmoina Phukon,Anil K Saikia","doi":"10.1021/acs.joc.5c02435","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02435","url":null,"abstract":"A novel SnCl4-mediated one-pot, three-component methodology has been developed for the direct synthesis of a diverse array of 4-aminoquinoline derivatives utilizing 2-aminobenzonitriles, aldehydes, and active methylene compounds. The reaction proceeds smoothly via a series of tandem reactions, including condensation followed by intramolecular cyclization and aromatization, to afford highly substituted 4-aminoquinolines in good to excellent yields (up to 88%) within 12-14 h. The protocol exhibits a broad substrate scope and excellent functional group tolerance. Notably, the strategy can also be applied for the construction of highly fused polycyclic frameworks through C-H activation and annulation and allows for the efficient synthesis of diacylated derivatives, highlighting its broad synthetic utility.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146089048","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Qi Shi,Dong-Xiang Li,Xing-Lan Wang,Yu-Rong Yang,Xin-Yu Zhang,Cheng-He Zhou,Zhong-Lin Zang,Gui-Xin Cai
This work reports a green and sustainable method of chlorohydroxylation of chalcone derivatives via visible-light-induced copper catalysis under room temperature conditions to chemoselectively convert chalcones into the corresponding chlorohydrins. This approach enables the efficient conversion of various chalcone derivatives with electron-withdrawing and electron-donating groups. Preliminary mechanistic studies indicated that chlorine radical (Cl·) generated through the ligand-to-metal charge transfer process can promote the efficient construction of chlorohydrin structures.
{"title":"Visible-Light-Driven Copper Catalysis: A Green and Sustainable Approach to Chlorohydroxylation of Chalcones.","authors":"Qi Shi,Dong-Xiang Li,Xing-Lan Wang,Yu-Rong Yang,Xin-Yu Zhang,Cheng-He Zhou,Zhong-Lin Zang,Gui-Xin Cai","doi":"10.1021/acs.joc.5c02788","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02788","url":null,"abstract":"This work reports a green and sustainable method of chlorohydroxylation of chalcone derivatives via visible-light-induced copper catalysis under room temperature conditions to chemoselectively convert chalcones into the corresponding chlorohydrins. This approach enables the efficient conversion of various chalcone derivatives with electron-withdrawing and electron-donating groups. Preliminary mechanistic studies indicated that chlorine radical (Cl·) generated through the ligand-to-metal charge transfer process can promote the efficient construction of chlorohydrin structures.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146089183","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Da-Liang Zhu,Jie Li,David James Young,Yanqing Wang,Chang Cheng,Hong-Xi Li
An efficient visible-light-induced copper-catalyzed decarboxylative (thio)esterification of α-keto acids with (thio)phenols has been developed using 2-chloro-thioxanthen-9-one as the photocatalyst and dimethyl sulfoxide (DMSO) as the terminal oxidant and solvent, enabling the efficient synthesis of aryl (thio)benzoates in moderate to excellent yields (66 examples). This operationally simple protocol exhibits excellent tolerance toward various functional groups, has been applied to the synthesis of pharmaceutical/natural product derivatives, and proceeds efficiently on a gram scale.
{"title":"Decarboxylative (Thio)esterification of α-Keto Acids via Carbonyl-Photoredox/Copper Dual Catalysis.","authors":"Da-Liang Zhu,Jie Li,David James Young,Yanqing Wang,Chang Cheng,Hong-Xi Li","doi":"10.1021/acs.joc.5c03066","DOIUrl":"https://doi.org/10.1021/acs.joc.5c03066","url":null,"abstract":"An efficient visible-light-induced copper-catalyzed decarboxylative (thio)esterification of α-keto acids with (thio)phenols has been developed using 2-chloro-thioxanthen-9-one as the photocatalyst and dimethyl sulfoxide (DMSO) as the terminal oxidant and solvent, enabling the efficient synthesis of aryl (thio)benzoates in moderate to excellent yields (66 examples). This operationally simple protocol exhibits excellent tolerance toward various functional groups, has been applied to the synthesis of pharmaceutical/natural product derivatives, and proceeds efficiently on a gram scale.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"74 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146073300","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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