We report a novel cyclic urea phosphonate ester as a newly developed reagent and its application in the Buchwald cross-coupling reactions for the synthesis of aromatic and heteroaromatic substituted ureas. This method enables the introduction of the cyclic urea moieties onto aromatic systems. Furthermore, these cyclic ureas are easily prepared and stored. The synthetic utility of this approach was successfully demonstrated through late-stage modification of the quinazoline core.
{"title":"Cyclic N-difluoromethyl urea phosphonate ester: A newly developed masked urea reagent for the CN coupling of aromatic/hetero aromatic halides","authors":"Reddi Shanmukha Rao , Manivannan Muthukumar , Arvind Mathur , Richland Tester , Bandari Chandrasekhar","doi":"10.1016/j.tetlet.2025.155935","DOIUrl":"10.1016/j.tetlet.2025.155935","url":null,"abstract":"<div><div>We report a novel cyclic urea phosphonate ester as a newly developed reagent and its application in the Buchwald cross-coupling reactions for the synthesis of aromatic and heteroaromatic substituted ureas. This method enables the introduction of the cyclic urea moieties onto aromatic systems. Furthermore, these cyclic ureas are easily prepared and stored. The synthetic utility of this approach was successfully demonstrated through late-stage modification of the quinazoline core.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155935"},"PeriodicalIF":1.5,"publicationDate":"2025-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145837871","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-23DOI: 10.1016/j.tetlet.2025.155950
Shan Lv , Hongxiang Tan , Xiaohui Jia , Yuntao Fan , Siyi Song , Feng He , Tianshu Kou , Zhihui Shao
Thiophene carboxylic acids are pivotal building blocks in medicinal and material chemistry. However, their synthesis relies on traditional stoichiometric oxidants or precious-metal catalysts, which are environmentally and economically concerning. This study reported a sustainable and atom-economical method for directly synthesizing thiophenic carboxylic acids using a manganese-catalyzed dehydrogenative coupling. A well-defined pincer Mn(I) complex as the catalyst was utilized to smoothly convert a wide range of thiophene alcohols and thiophene aldehydes to the corresponding carboxylic acids with the liberation of H2 as the sole byproduct. The protocol exhibited excellent functional group tolerance and high efficiency. Additionally, the bifunctional thiophene alcohols or thiophene aldehydes could be efficiently converted into dicarboxylic acid products under optimal reaction conditions. This study provided a green and practical alternative to the existing methodologies.
{"title":"Pincer manganese-catalyzed dehydrogenative synthesis of thiophene carboxylic acids from thiophene alcohols and aldehydes","authors":"Shan Lv , Hongxiang Tan , Xiaohui Jia , Yuntao Fan , Siyi Song , Feng He , Tianshu Kou , Zhihui Shao","doi":"10.1016/j.tetlet.2025.155950","DOIUrl":"10.1016/j.tetlet.2025.155950","url":null,"abstract":"<div><div>Thiophene carboxylic acids are pivotal building blocks in medicinal and material chemistry. However, their synthesis relies on traditional stoichiometric oxidants or precious-metal catalysts, which are environmentally and economically concerning. This study reported a sustainable and atom-economical method for directly synthesizing thiophenic carboxylic acids using a manganese-catalyzed dehydrogenative coupling. A well-defined pincer Mn(I) complex as the catalyst was utilized to smoothly convert a wide range of thiophene alcohols and thiophene aldehydes to the corresponding carboxylic acids with the liberation of H<sub>2</sub> as the sole byproduct. The protocol exhibited excellent functional group tolerance and high efficiency. Additionally, the bifunctional thiophene alcohols or thiophene aldehydes could be efficiently converted into dicarboxylic acid products under optimal reaction conditions. This study provided a green and practical alternative to the existing methodologies.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155950"},"PeriodicalIF":1.5,"publicationDate":"2025-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922014","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The catalytic transformation of 2-(2-aminophenyl)ethanol with arylmethanols has emerged as a versatile and atom-economical route for constructing indole-based heterocycles. Over the past decade, systematic advances have revealed that catalyst design and reaction conditions critically dictate product selectivity, enabling access to C3-alkylated, N-alkylated, bis(indolyl)methanes (BIMs), formylated indoles, and 3-hydroxyindolin-2-ones. Early reports predominantly yielded C3-alkylated indoles, while subsequent developments employing rationally designed pincer-type complexes of Ru(II), Zn(II), Fe(II), Co(II), Mn(I), and Ni(II) have demonstrated a remarkable divergence in reactivity. Notably, Ni–dcype catalysis enabled a selective N-alkylation pathway, whereas the Co(II)–NNSe complex achieved the first one-pot synthesis of 2-aryl-3-formylindoles. Furthermore, variation in catalyst design, such as Ru–NNN pincer systems, afforded structurally complex 3-hydroxyindolin-2-ones under controlled oxidation conditions. These examples highlight how subtle modifications in the electronic and structural features of catalysts direct mechanistic routes through imine formation, hydrogen transfer, or oxidative cyclization. This review underscores the interplay between catalyst architecture, base selection, and reaction environment in governing chemoselectivity and provides mechanistic insights guiding the design of sustainable, earth-abundant metal catalysts for selective indole synthesis.
{"title":"Divergent catalytic routes to indoles from 2-(aminophenyl)ethanol and arylmethanols: insights into mechanism and selectivity","authors":"Sohan Singh , Suman Mahala , Harsh Sharma, Mayank Shekhawat, Hemant Joshi","doi":"10.1016/j.tetlet.2025.155951","DOIUrl":"10.1016/j.tetlet.2025.155951","url":null,"abstract":"<div><div>The catalytic transformation of 2-(2-aminophenyl)ethanol with arylmethanols has emerged as a versatile and atom-economical route for constructing indole-based heterocycles. Over the past decade, systematic advances have revealed that catalyst design and reaction conditions critically dictate product selectivity, enabling access to <em>C3-</em>alkylated, <em>N</em>-alkylated, bis(indolyl)methanes (BIMs), formylated indoles, and 3-hydroxyindolin-2-ones. Early reports predominantly yielded <em>C3-</em>alkylated indoles, while subsequent developments employing rationally designed pincer-type complexes of Ru(II), Zn(II), Fe(II), Co(II), Mn(I), and Ni(II) have demonstrated a remarkable divergence in reactivity. Notably, Ni–dcype catalysis enabled a selective <em>N</em>-alkylation pathway, whereas the Co(II)–NNSe complex achieved the first one-pot synthesis of 2-aryl-3-formylindoles. Furthermore, variation in catalyst design, such as Ru–NNN pincer systems, afforded structurally complex 3-hydroxyindolin-2-ones under controlled oxidation conditions. These examples highlight how subtle modifications in the electronic and structural features of catalysts direct mechanistic routes through imine formation, hydrogen transfer, or oxidative cyclization. This review underscores the interplay between catalyst architecture, base selection, and reaction environment in governing chemoselectivity and provides mechanistic insights guiding the design of sustainable, earth-abundant metal catalysts for selective indole synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155951"},"PeriodicalIF":1.5,"publicationDate":"2025-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145837874","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-23DOI: 10.1016/j.tetlet.2025.155952
Wei Jiang , Guanghui Fan , Zhijiang Ma , Zhaozhi Zhu , Gege Zhao , Pengpeng Gao , Peiwen Yang , Jiangang Gan , Hongbo Wei , Weiqing Xie
Arcutine diterpenoid alkaloids are a subclass of C20-diterpenoid alkaloids characterized by a unique tetracyclo[5.3.3.04,9.04,12]tridecane framework. Herein, we report a facile strategy for constructing this scaffold through a tandem Diels–Alder/retro-Diels–Alder/Diels–Alder sequence using 2H-pyran-2-one derivatives bearing two terminal alkenes. DFT studies were also conducted to elucidate the reaction mechanism, revealing that CO2 extrusion plays a crucial role in driving the formation of the diene intermediate, which smoothly undergoes the second Diels–Alder cycloaddition.
{"title":"Synthetic study of arcutine diterpenoid alkaloids: rapid construction of tetracyclo[5.3.3.04,9.04,12]tridecane framework via intramolecular Diels–Alder/retro-Diels–Alder/Diels–Alder cascade","authors":"Wei Jiang , Guanghui Fan , Zhijiang Ma , Zhaozhi Zhu , Gege Zhao , Pengpeng Gao , Peiwen Yang , Jiangang Gan , Hongbo Wei , Weiqing Xie","doi":"10.1016/j.tetlet.2025.155952","DOIUrl":"10.1016/j.tetlet.2025.155952","url":null,"abstract":"<div><div>Arcutine diterpenoid alkaloids are a subclass of C20-diterpenoid alkaloids characterized by a unique tetracyclo[5.3.3.0<sup>4,9</sup>.0<sup>4,12</sup>]tridecane framework. Herein, we report a facile strategy for constructing this scaffold through a tandem Diels–Alder/<em>retro</em>-Diels–Alder/Diels–Alder sequence using 2<em>H</em>-pyran-2-one derivatives bearing two terminal alkenes. DFT studies were also conducted to elucidate the reaction mechanism, revealing that CO<sub>2</sub> extrusion plays a crucial role in driving the formation of the diene intermediate, which smoothly undergoes the second Diels–Alder cycloaddition.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155952"},"PeriodicalIF":1.5,"publicationDate":"2025-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881189","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-21DOI: 10.1016/j.tetlet.2025.155944
Yiping Huang , Changhai Yue , Dan Wu , Yufan Ji , Kai Zhu , Lei Fan , Wenyu Zhang , Hong Qin , Zheng Fang
An efficient one-pot heptafluoroisopropyl iodide/silver(I)-mediated cross-dehydrogenative N–H/benzylic C(sp3)–H coupling of benzimidazoles with simple benzylic hydrocarbons has been developed. This protocol enables the direct construction of CN bonds from readily available substrates without prefunctionalization under mild conditions. Under the optimized conditions (Ag₂O as the oxidant and i-C₃F₇I as a radical precursor, 100 °C, air), a broad range of N-alkylated benzimidazoles and related azoles are obtained in moderate to good yields with good tolerance to various functional groups. Mechanistic studies, including radical inhibition experiments and a kinetic isotope effect (k_H/k_D = 2.1), support a radical pathway in which benzylic and N-centered radicals are generated under fluorinated radical/silver(I) initiation and undergo radical–radical cross-coupling to form the CN bond. This straightforward and operationally simple strategy provides a practical and complementary approach for the synthesis of benzimidazole derivatives via direct benzylic C(sp3)–H amination.
{"title":"Heptafluoroisopropyl iodide/silver(I)-mediated benzylic C(sp3)–H amination: direct access to N-alkylated benzimidazoles from simple hydrocarbons","authors":"Yiping Huang , Changhai Yue , Dan Wu , Yufan Ji , Kai Zhu , Lei Fan , Wenyu Zhang , Hong Qin , Zheng Fang","doi":"10.1016/j.tetlet.2025.155944","DOIUrl":"10.1016/j.tetlet.2025.155944","url":null,"abstract":"<div><div>An efficient one-pot heptafluoroisopropyl iodide/silver(I)-mediated cross-dehydrogenative N–H/benzylic C(sp<sup>3</sup>)–H coupling of benzimidazoles with simple benzylic hydrocarbons has been developed. This protocol enables the direct construction of C<img>N bonds from readily available substrates without prefunctionalization under mild conditions. Under the optimized conditions (Ag₂O as the oxidant and i-C₃F₇I as a radical precursor, 100 °C, air), a broad range of N-alkylated benzimidazoles and related azoles are obtained in moderate to good yields with good tolerance to various functional groups. Mechanistic studies, including radical inhibition experiments and a kinetic isotope effect (k_H/k_D = 2.1), support a radical pathway in which benzylic and N-centered radicals are generated under fluorinated radical/silver(I) initiation and undergo radical–radical cross-coupling to form the C<img>N bond. This straightforward and operationally simple strategy provides a practical and complementary approach for the synthesis of benzimidazole derivatives via direct benzylic C(sp<sup>3</sup>)–H amination.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155944"},"PeriodicalIF":1.5,"publicationDate":"2025-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145837939","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-20DOI: 10.1016/j.tetlet.2025.155945
Jacob C. Hood, Douglas A. Klumpp
A series of N-heterocyclic-substituted cyclopropyl ethanols were prepared and shown to give excellent product conversions in Friedel-Crafts reactions with benzene in trifluoromethanesulfonic acid (triflic acid). With protonation of the N-heterocycle and ionization of the cyclopropylcarbinol, dicationic species are generated. These provide homoallyl products (93–99 % yields) and with heating give substituted-tetralin products (84–97 % yields).
{"title":"Temperature-controlled Friedel-Crafts reactions of cyclopropyl ethanols via dicationic bicyclobutonium ion intermediates","authors":"Jacob C. Hood, Douglas A. Klumpp","doi":"10.1016/j.tetlet.2025.155945","DOIUrl":"10.1016/j.tetlet.2025.155945","url":null,"abstract":"<div><div>A series of <em>N</em>-heterocyclic-substituted cyclopropyl ethanols were prepared and shown to give excellent product conversions in Friedel-Crafts reactions with benzene in trifluoromethanesulfonic acid (triflic acid). With protonation of the N-heterocycle and ionization of the cyclopropylcarbinol, dicationic species are generated. These provide homoallyl products (93–99 % yields) and with heating give substituted-tetralin products (84–97 % yields).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155945"},"PeriodicalIF":1.5,"publicationDate":"2025-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881320","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-19DOI: 10.1016/j.tetlet.2025.155943
Ian P. Shire, Zarko Boskovic
Heating oxiranes with Lawesson's reagent in aromatic solvents results in the formation of thiophosphonothioates. The reaction proceeds most efficiently with substrates where elimination is hindered by their geometry. The observed regioselectivity can be explained by cation stabilization in bicyclic systems. In particular, electron-donating groups significantly enhance the stabilization of carbocations at the homobenzylic position in rigid bicyclic frameworks.
{"title":"Thiophosphonothioates from oxiranes","authors":"Ian P. Shire, Zarko Boskovic","doi":"10.1016/j.tetlet.2025.155943","DOIUrl":"10.1016/j.tetlet.2025.155943","url":null,"abstract":"<div><div>Heating oxiranes with Lawesson's reagent in aromatic solvents results in the formation of thiophosphonothioates. The reaction proceeds most efficiently with substrates where elimination is hindered by their geometry. The observed regioselectivity can be explained by cation stabilization in bicyclic systems. In particular, electron-donating groups significantly enhance the stabilization of carbocations at the homobenzylic position in rigid bicyclic frameworks.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155943"},"PeriodicalIF":1.5,"publicationDate":"2025-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145837873","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-19DOI: 10.1016/j.tetlet.2025.155932
Ichrak Souii , Momtez Jmaï , Jesús M. de los Santos , Hédi M'Rabet
Interest in the synthetic routes to aminobisphosphonates has been steadily increasing due to their wide range of applications. In this work, we report a novel approach for the preparation of two series of non-symmetric allylic aminobisphosphonates under mild reaction conditions. The target compounds were obtained via nucleophilic substitution of α-aminophosphonates with two different phosphonated bromine derivatives: 2-bromoethyl diethyl phosphonate and ethyl 2-(bromomethyl)-3-(diethoxyphosphoryl)acrylate. In the case of N-(phosphorylmethyl)-N-(2-phosphorylethyl) allylamines, the allyl fragment originates from allyl-substituted α-aminophosphonates, whereas for N-(phosphorylmethyl)-3-phosphorylallylamine, it is introduced through the ethyl 2-(bromomethyl)-3-(diethoxyphosphoryl)acrylate synthon.
{"title":"Non-symmetrical Bisphosphonated allylic amines: unprecedented synthesis from α-aminomonophosphonates","authors":"Ichrak Souii , Momtez Jmaï , Jesús M. de los Santos , Hédi M'Rabet","doi":"10.1016/j.tetlet.2025.155932","DOIUrl":"10.1016/j.tetlet.2025.155932","url":null,"abstract":"<div><div>Interest in the synthetic routes to aminobisphosphonates has been steadily increasing due to their wide range of applications. In this work, we report a novel approach for the preparation of two series of non-symmetric allylic aminobisphosphonates under mild reaction conditions. The target compounds were obtained via nucleophilic substitution of α-aminophosphonates with two different phosphonated bromine derivatives: 2-bromoethyl diethyl phosphonate and ethyl 2-(bromomethyl)-3-(diethoxyphosphoryl)acrylate. In the case of <em>N</em>-(phosphorylmethyl)-<em>N</em>-(2-phosphorylethyl) allylamines, the allyl fragment originates from allyl-substituted α-aminophosphonates, whereas for <em>N</em>-(phosphorylmethyl)-3-phosphorylallylamine, it is introduced through the ethyl 2-(bromomethyl)-3-(diethoxyphosphoryl)acrylate synthon.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155932"},"PeriodicalIF":1.5,"publicationDate":"2025-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145789149","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-18DOI: 10.1016/j.tetlet.2025.155936
P. Krishna Rao , T. Gowthami , P. Narayana Reddy , B. Sridhar , B.V. Subba Reddy , P. Padmaja
We established a strategy for triazole directed, rhodium-catalyzed regio-ortho-selective CH alkylation of 2-aryl-1,2,3-triazoles with maleimides. This transformation provided a straightforward approach for the synthesis of biologically important succinimide-triazole hybrid molecules in moderate to good yields with good functional group compatibility. This method avoids the tedious pre-synthesis of 2-aryl-1,2,3-triazole N-oxide precursor.
{"title":"Highly regioselective alkylation of 2-aryl-1,2,3-triazoles with maleimides through ortho-CH functionalization","authors":"P. Krishna Rao , T. Gowthami , P. Narayana Reddy , B. Sridhar , B.V. Subba Reddy , P. Padmaja","doi":"10.1016/j.tetlet.2025.155936","DOIUrl":"10.1016/j.tetlet.2025.155936","url":null,"abstract":"<div><div>We established a strategy for triazole directed, rhodium-catalyzed regio-<em>ortho</em>-selective C<img>H alkylation of 2-aryl-1,2,3-triazoles with maleimides. This transformation provided a straightforward approach for the synthesis of biologically important succinimide-triazole hybrid molecules in moderate to good yields with good functional group compatibility. This method avoids the tedious pre-synthesis of 2-aryl-1,2,3-triazole <em>N</em>-oxide precursor.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155936"},"PeriodicalIF":1.5,"publicationDate":"2025-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881190","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-12-17DOI: 10.1016/j.tetlet.2025.155928
Han-Chi Wang, Zhi-Xue Song, Na-Na Sun, Bo Sun
A Ru(II)-catalyzed ortho allylation of N-aryl-7-azaindoles with readily accessible vinylcyclopropanes has been developed. This methodology facilitates the efficient construction of C(sp2)-C(sp3) bonds through sequential CH and CC activation, providing a concise and highly efficient route (up to 93 % yield) to valuable 7-azaindole derivatives. Furthermore, the strategy has been successfully extended to the allylation of isoquinolones with vinylcyclopropanes, underscoring the broad applicability and practical value of this synthetic approach.
{"title":"Ru(II)-catalyzed ortho CH allylation of N-aryl-7-azaindoles with vinylcyclopropanes","authors":"Han-Chi Wang, Zhi-Xue Song, Na-Na Sun, Bo Sun","doi":"10.1016/j.tetlet.2025.155928","DOIUrl":"10.1016/j.tetlet.2025.155928","url":null,"abstract":"<div><div>A Ru(II)-catalyzed <em>ortho</em> allylation of <em>N</em>-aryl-7-azaindoles with readily accessible vinylcyclopropanes has been developed. This methodology facilitates the efficient construction of C(sp<sup>2</sup>)-C(sp<sup>3</sup>) bonds through sequential C<img>H and C<img>C activation, providing a concise and highly efficient route (up to 93 % yield) to valuable 7-azaindole derivatives. Furthermore, the strategy has been successfully extended to the allylation of isoquinolones with vinylcyclopropanes, underscoring the broad applicability and practical value of this synthetic approach.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155928"},"PeriodicalIF":1.5,"publicationDate":"2025-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145837875","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
扫码关注我们
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号