Jun Pan , Yuting Feng , Huijun Qian , Leiyang Lv , Zhiping Li
Oxygen-centered radicals are highly reactive intermediates that serve key roles in radical-mediated organic transformations. Carbonyloxy radicals, a distinct subset of oxygen-centered radicals, not only exhibit the general reactivity patterns of oxygen-centered species, such as hydrogen atom transfer (HAT) and β-scission, but also demonstrate unique behaviors attributed to their electrophilic ester group. In this review, we summarize recent progress in the intermolecular addition of aryl and alkoxy carbonyloxy radicals to alkenes through different precursors of carbonyloxy radicals. These transformations highlight novel esterification reactions, in which generally alcohols react with carboxylic acids, acyl chlorides, or acid anhydrides. We aim to inspire further exploration into the innovative esterification reactions enabled by carbonyloxy radical chemistry.
{"title":"Recent advances in the intermolecular addition of carbonyloxy radicals to alkenes","authors":"Jun Pan , Yuting Feng , Huijun Qian , Leiyang Lv , Zhiping Li","doi":"10.1039/d5qo01045d","DOIUrl":"10.1039/d5qo01045d","url":null,"abstract":"<div><div>Oxygen-centered radicals are highly reactive intermediates that serve key roles in radical-mediated organic transformations. Carbonyloxy radicals, a distinct subset of oxygen-centered radicals, not only exhibit the general reactivity patterns of oxygen-centered species, such as hydrogen atom transfer (HAT) and β-scission, but also demonstrate unique behaviors attributed to their electrophilic ester group. In this review, we summarize recent progress in the intermolecular addition of aryl and alkoxy carbonyloxy radicals to alkenes through different precursors of carbonyloxy radicals. These transformations highlight novel esterification reactions, in which generally alcohols react with carboxylic acids, acyl chlorides, or acid anhydrides. We aim to inspire further exploration into the innovative esterification reactions enabled by carbonyloxy radical chemistry.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6698-6716"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144919432","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}
Over the past few years, there has been exponential progress in the synthesis of value-added molecules utilizing nitroso compounds. The reactions of nitroso compounds with economically cheap reactive precursors have drawn much interest from organic chemists across the globe due to their high regioselectivities; enantioselectivities; and efficiencies for annulation, C–H activations, cycloaddition, Diels–Alder reaction, and notable metal-free reactions. In particular, the nitroso moiety has recently emerged as a powerful synthon and transformable directing group in direct C–H functionalization reactions. In this review, we have broadly discussed recent reports on the versatile applications of nitroso compounds as useful building blocks in the selective synthesis of a diverse range of molecules.
{"title":"Nitrosobenzenes as a stepping stone for the development of transition metal and metal-free organic transformations: a comprehensive review","authors":"Nandini R. , Ramesh B. Dateer","doi":"10.1039/d5qo00842e","DOIUrl":"10.1039/d5qo00842e","url":null,"abstract":"<div><div>Over the past few years, there has been exponential progress in the synthesis of value-added molecules utilizing nitroso compounds. The reactions of nitroso compounds with economically cheap reactive precursors have drawn much interest from organic chemists across the globe due to their high regioselectivities; enantioselectivities; and efficiencies for annulation, C–H activations, cycloaddition, Diels–Alder reaction, and notable metal-free reactions. In particular, the nitroso moiety has recently emerged as a powerful synthon and transformable directing group in direct C–H functionalization reactions. In this review, we have broadly discussed recent reports on the versatile applications of nitroso compounds as useful building blocks in the selective synthesis of a diverse range of molecules.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6717-6780"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145077872","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}
Ying Fu , Hao Chen , Yu Luo , Wenying Yang , Liying Jia , Zhengyin Du
A palladium-catalyzed decarboxylative annulation reaction of 2-iodobenzimines with 2-halobenzoic acids has been developed for the synthesis of phenanthridine scaffolds. Density functional theory calculations revealed that in the presence of the KOAc additive, this annulation reaction proceeds via a Pd(ii) transmetalation pathway rather than the oxidative Pd(iv) formation pathway. The base Cs2CO3 plays a crucial role in C–H bond activation, which is the rate-determining step.
{"title":"Synthesis of phenanthridines via a palladium-catalyzed annulation of 2-iodobenzimines with 2-halobenzoic acids","authors":"Ying Fu , Hao Chen , Yu Luo , Wenying Yang , Liying Jia , Zhengyin Du","doi":"10.1039/d5qo00968e","DOIUrl":"10.1039/d5qo00968e","url":null,"abstract":"<div><div>A palladium-catalyzed decarboxylative annulation reaction of 2-iodobenzimines with 2-halobenzoic acids has been developed for the synthesis of phenanthridine scaffolds. Density functional theory calculations revealed that in the presence of the KOAc additive, this annulation reaction proceeds <em>via</em> a Pd(<span>ii</span>) transmetalation pathway rather than the oxidative Pd(<span>iv</span>) formation pathway. The base Cs<sub>2</sub>CO<sub>3</sub> plays a crucial role in C–H bond activation, which is the rate-determining step.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6433-6442"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144802930","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}
Yutong Sun , Wenlin Zhang , Ying Liu , Zhixin Zhang , Mengyao Hu , Xiaoguang Liu , Hongbo Qin , Helin Lu
The C2-methylated indole scaffolds are prevalent and crucial components of numerous pharmaceutical molecules and biologically active entities. However, their synthesis traditionally requires a laborious three-step sequence involving the installation of suitable directing groups, C2-functionalization, and deprotection. Herein, we report a one-step, regioselective C2–H methylation of free (N–H) indoles via Pd(ii)/norbornene(NBE) catalysis using trimethyl phosphate as a practical methyl source. This modular methodology uniquely circumvents previous multi-step strategies, demonstrating broad applicability with excellent functional group tolerance, high to quantitative yields, robust scalability, successful trideuteromethylation, and operational simplicity due to its air and moisture insensitivity. This step-economical strategy significantly streamlines access to valuable C2-methylated indole derivatives, offering a more direct and efficient pathway for late-stage methylation of drug-like indoles compared to previous methods.
{"title":"Regioselective one-step C2–H methylation of free (N–H) indoles enabled by Pd(ii)/norbornene cooperative catalysis","authors":"Yutong Sun , Wenlin Zhang , Ying Liu , Zhixin Zhang , Mengyao Hu , Xiaoguang Liu , Hongbo Qin , Helin Lu","doi":"10.1039/d5qo00869g","DOIUrl":"10.1039/d5qo00869g","url":null,"abstract":"<div><div>The C2-methylated indole scaffolds are prevalent and crucial components of numerous pharmaceutical molecules and biologically active entities. However, their synthesis traditionally requires a laborious three-step sequence involving the installation of suitable directing groups, C2-functionalization, and deprotection. Herein, we report a one-step, regioselective C2–H methylation of free (<em>N</em>–H) indoles <em>via</em> Pd(<span>ii</span>)/norbornene(NBE) catalysis using trimethyl phosphate as a practical methyl source. This modular methodology uniquely circumvents previous multi-step strategies, demonstrating broad applicability with excellent functional group tolerance, high to quantitative yields, robust scalability, successful trideuteromethylation, and operational simplicity due to its air and moisture insensitivity. This step-economical strategy significantly streamlines access to valuable C2-methylated indole derivatives, offering a more direct and efficient pathway for late-stage methylation of drug-like indoles compared to previous methods.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6415-6422"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144819687","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}
Ke Xu , Kejun Lin , Jiayi Zhao , Jingmei Zeng , Tingshun Zhu
The N-heterocyclic carbene organocatalyzed δ-LUMO activation strategy was used for the atroposelective [5 + 5] construction of benzo[c]chromenone and phenanthridinone. The reaction cascade involved a regioselective and stereoselective 1,6-addition, an intramolecular aldol reaction, a chemoselective lactonization, dehydration, and successive oxidative aromatization accompanied by a simultaneous point-to-axial chirality transfer process. Axially chiral biaryls with gradient rotation barriers were synthesized and investigated. The multicyclic aromatic products can be obtained on a gram scale and further transformed into several interesting molecules. This study further expands the organocatalyzed benzannulation methods to the construction of more sophisticated multicyclic aromatics.
{"title":"Atroposelective [5 + 5] formation of benzo[c]chromenone and phenanthridinone by carbene organocatalysis","authors":"Ke Xu , Kejun Lin , Jiayi Zhao , Jingmei Zeng , Tingshun Zhu","doi":"10.1039/d5qo00986c","DOIUrl":"10.1039/d5qo00986c","url":null,"abstract":"<div><div>The N-heterocyclic carbene organocatalyzed δ-LUMO activation strategy was used for the atroposelective [5 + 5] construction of benzo[<em>c</em>]chromenone and phenanthridinone. The reaction cascade involved a regioselective and stereoselective 1,6-addition, an intramolecular aldol reaction, a chemoselective lactonization, dehydration, and successive oxidative aromatization accompanied by a simultaneous point-to-axial chirality transfer process. Axially chiral biaryls with gradient rotation barriers were synthesized and investigated. The multicyclic aromatic products can be obtained on a gram scale and further transformed into several interesting molecules. This study further expands the organocatalyzed benzannulation methods to the construction of more sophisticated multicyclic aromatics.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6472-6479"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144825198","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}
Giovanni Preda , Sonia La Cognata , Laura Pedraza-González , Laurine Carlier , Maxime Kolb , Gennaro Pescitelli , Valeria Amendola , Dominique Armspach , Dario Pasini
Molecular structures comprising naturally-occurring, stereodefined cyclodextrins and binaphthyls as bridging units have been realized, designed in such a way that the stereocommunication mode between the two chiral entities is unfavourable (‘chiral mismatch’). The induced strain translates into highly responsive chiroptical behavior. On one side, the binaphthol-containing structure functions as a pH-controlled, single-molecule chiroptical switch, with reversal of the optical activity from acidic to basic conditions in a fully reversible manner. Additionally, the same host molecule demonstrates a pronounced chiroptical response to perrhenate in aqueous solution at pH 2.5, showing excellent selectivity for this specific anion. Computational analysis confirmed that the major effect of ReO4− complexation is making new conformations accessible to the binaphthol moiety with a large variation of the associated dihedral angles.
{"title":"Manipulating stereo-communication in binaphthol-bridged α- and β-cyclodextrins to develop β-selective chiroptical pH switching and anion sensing in water","authors":"Giovanni Preda , Sonia La Cognata , Laura Pedraza-González , Laurine Carlier , Maxime Kolb , Gennaro Pescitelli , Valeria Amendola , Dominique Armspach , Dario Pasini","doi":"10.1039/d5qo00910c","DOIUrl":"10.1039/d5qo00910c","url":null,"abstract":"<div><div>Molecular structures comprising naturally-occurring, stereodefined cyclodextrins and binaphthyls as bridging units have been realized, designed in such a way that the stereocommunication mode between the two chiral entities is unfavourable (‘chiral mismatch’). The induced strain translates into highly responsive chiroptical behavior. On one side, the binaphthol-containing structure functions as a pH-controlled, single-molecule chiroptical switch, with reversal of the optical activity from acidic to basic conditions in a fully reversible manner. Additionally, the same host molecule demonstrates a pronounced chiroptical response to perrhenate in aqueous solution at pH 2.5, showing excellent selectivity for this specific anion. Computational analysis confirmed that the major effect of ReO<sub>4</sub><sup>−</sup> complexation is making new conformations accessible to the binaphthol moiety with a large variation of the associated dihedral angles.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6450-6459"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144857933","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}
Weikang Li , Zhe Chen , Chuanyi Xiong , Zhenjie Yang , Ning Wang , Peifeng Su , Yaru Jing , Haihua Huang , Zhuofeng Ke
The green reductive transformation of thioamides is highly desired yet faces challenges in broad substrate scope and selectivity for CS and C–N cleavage. Existing catalytic hydrogenation methods are still limited and require harsh reaction conditions. Here, computation-aided design discovered a catalyst-free protocol for thioamides’ reductive desulfurization with ammonia borane (AB). The system uses dimethylamine-borane (DMAB) to directly reduce thioamides to amines under catalyst-free, practical, economical, green, and easy-to-handle conditions. It covers a broad scope for primary, secondary, and tertiary thioamides. The experimental and theoretical studies revealed a concerted double-hydrogen transfer mechanism for this catalyst-free system, in which DMAB was found to play an important self-catalytic role in the reaction. This practical and selective protocol provides an important example for designing catalyst-free reductive systems.
{"title":"Catalyst-free reductive desulfurization of thioamides with ammonia borane through a concerted double-hydrogen transfer mechanism","authors":"Weikang Li , Zhe Chen , Chuanyi Xiong , Zhenjie Yang , Ning Wang , Peifeng Su , Yaru Jing , Haihua Huang , Zhuofeng Ke","doi":"10.1039/d5qo01028d","DOIUrl":"10.1039/d5qo01028d","url":null,"abstract":"<div><div>The green reductive transformation of thioamides is highly desired yet faces challenges in broad substrate scope and selectivity for CS and C–N cleavage. Existing catalytic hydrogenation methods are still limited and require harsh reaction conditions. Here, computation-aided design discovered a catalyst-free protocol for thioamides’ reductive desulfurization with ammonia borane (AB). The system uses dimethylamine-borane (DMAB) to directly reduce thioamides to amines under catalyst-free, practical, economical, green, and easy-to-handle conditions. It covers a broad scope for primary, secondary, and tertiary thioamides. The experimental and theoretical studies revealed a concerted double-hydrogen transfer mechanism for this catalyst-free system, in which DMAB was found to play an important self-catalytic role in the reaction. This practical and selective protocol provides an important example for designing catalyst-free reductive systems.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6423-6432"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144792404","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}
In recent years, transition-metal hydride catalysis has emerged as a powerful strategy for radical Markovnikov hydrothiolation of alkenes, providing efficient access to branched thioethers. However, this approach remains underexplored, with existing methods often hampered by limitations such as the reliance on silane reductants, the need for specialized sulfide nucleophiles or radical acceptors, or the use of external oxidants. Herein, we report a new light-promoted cobalt-catalyzed system that employs Hantzsch ester as a mild hydride source for the radical Markovnikov hydrothiolation of alkenes using N-arylsulfenyl phthalimides as thiyl radical precursors. Notably, when allylic arenes were employed as substrates, a metal-hydride hydrogen atom transfer (MHAT)/retro-MHAT process occurred, enabling the synthesis of branched benzyl sulfides, which was unattainable under conventional catalytic conditions. Mechanistic investigations support the proposed reaction pathway. This method exhibits excellent regioselectivity, broad functional group compatibility, and applicability in late-stage functionalization.
{"title":"Light-promoted cobalt-catalyzed radical Markovnikov hydrothiolation of alkenes with N-arylsulfenyl phthalimides","authors":"Xiang-Rui Li , Rong-Jin Zhang , Ting-Ting Miao , Yonghong Xiao , Kun-Quan Chen , Jian-Ji Zhong","doi":"10.1039/d5qo01020a","DOIUrl":"10.1039/d5qo01020a","url":null,"abstract":"<div><div>In recent years, transition-metal hydride catalysis has emerged as a powerful strategy for radical Markovnikov hydrothiolation of alkenes, providing efficient access to branched thioethers. However, this approach remains underexplored, with existing methods often hampered by limitations such as the reliance on silane reductants, the need for specialized sulfide nucleophiles or radical acceptors, or the use of external oxidants. Herein, we report a new light-promoted cobalt-catalyzed system that employs Hantzsch ester as a mild hydride source for the radical Markovnikov hydrothiolation of alkenes using <em>N</em>-arylsulfenyl phthalimides as thiyl radical precursors. Notably, when allylic arenes were employed as substrates, a metal-hydride hydrogen atom transfer (MHAT)/<em>retro</em>-MHAT process occurred, enabling the synthesis of branched benzyl sulfides, which was unattainable under conventional catalytic conditions. Mechanistic investigations support the proposed reaction pathway. This method exhibits excellent regioselectivity, broad functional group compatibility, and applicability in late-stage functionalization.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6548-6555"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144898832","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}
Anee Taj , Chen Cui , Zhenwei Shi , Xuebin Huang , Xiao-Hui Yang
Catalytic hydroselenation of alkenes represents one of the most direct and efficient methods for organoselenide synthesis. In this study, we report a highly regioselective Rh-catalyzed hydroselenation of unsymmetric 1,3-dienes, including internal unsymmetric dienes. This atom-economical method operates under mild conditions and selectively affords 3,4-Markovnikov products with excellent regiocontrol. The developed protocol was effective in reactions involving both internal and terminal dienes.
{"title":"Rhodium-catalyzed hydroselenation of unsymmetric 1,3-dienes with 3,4-Markovnikov regioselectivity","authors":"Anee Taj , Chen Cui , Zhenwei Shi , Xuebin Huang , Xiao-Hui Yang","doi":"10.1039/d5qo00926j","DOIUrl":"10.1039/d5qo00926j","url":null,"abstract":"<div><div>Catalytic hydroselenation of alkenes represents one of the most direct and efficient methods for organoselenide synthesis. In this study, we report a highly regioselective Rh-catalyzed hydroselenation of unsymmetric 1,3-dienes, including internal unsymmetric dienes. This atom-economical method operates under mild conditions and selectively affords 3,4-Markovnikov products with excellent regiocontrol. The developed protocol was effective in reactions involving both internal and terminal dienes.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6401-6406"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144840265","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}
Hongxiang Huang , Ruimeng Zhang , Leiqing Fu , Jie-Ping Wan
The Rh-catalyzed C–H activation of N-pyridinyl enaminones and cascade cyclization with diazo compounds are reported to construct 2-pyrones and pyrido-quinazolinones with a broad range of substrates and good yields. The use of NaOAc as the additive and HFIP as the solvent affords 2-pyrones via C–H bond activation, enolization type conversion and cyclization. On the other hand, the use of NaOPiv and AgNTf2 as the additives and TFE as the solvent leads to pyrido-quinazolinones based on C–H bond activation, Knoevenagel condensation, aromatization and cyclization.
{"title":"Rh(iii)-catalyzed cascade cyclization of enaminones with diazo compounds: switchable syntheses of 2-pyrones and pyrido-quinazolinones","authors":"Hongxiang Huang , Ruimeng Zhang , Leiqing Fu , Jie-Ping Wan","doi":"10.1039/d5qo01086a","DOIUrl":"10.1039/d5qo01086a","url":null,"abstract":"<div><div>The Rh-catalyzed C–H activation of <em>N</em>-pyridinyl enaminones and cascade cyclization with diazo compounds are reported to construct 2-pyrones and pyrido-quinazolinones with a broad range of substrates and good yields. The use of NaOAc as the additive and HFIP as the solvent affords 2-pyrones <em>via</em> C–H bond activation, enolization type conversion and cyclization. On the other hand, the use of NaOPiv and AgNTf<sub>2</sub> as the additives and TFE as the solvent leads to pyrido-quinazolinones based on C–H bond activation, Knoevenagel condensation, aromatization and cyclization.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 23","pages":"Pages 6602-6608"},"PeriodicalIF":0.0,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144930879","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}
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