Beilstein Journal of Organic Chemistry最新文献_第2页

Homogeneous copper-catalyzed aerobic oxidation of alcohols and aldehydes: mechanistic insights and recent advances. 均相铜催化醇和醛的有氧氧化：机理的见解和最新进展。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-29 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.107

Hristo Petkov, Svilen P Simeonov

{"title":"Homogeneous copper-catalyzed aerobic oxidation of alcohols and aldehydes: mechanistic insights and recent advances.","authors":"Hristo Petkov, Svilen P Simeonov","doi":"10.3762/bjoc.22.107","DOIUrl":"https://doi.org/10.3762/bjoc.22.107","url":null,"abstract":"Copper-catalyzed aerobic oxidation of alcohols and aldehydes has become a key transformation for the sustainable synthesis of carbonyl compounds, combining high efficiency with the use of molecular oxygen as a benign terminal oxidant. Owing to its earth-abundance, low cost, low toxicity, and versatile redox properties, copper offers a compelling alternative to traditional noble metal catalysts and stoichiometric oxidation methods. This review highlights the evolution of copper-catalyzed aerobic oxidation of alcohols, emphasizing two distinct mechanistic regimes: nitroxyl radical-mediated systems and nitroxyl-free pathways, in which copper-ligand complexes directly promote dioxygen activation and substrate oxidation. Methods for conversion of aldehydes to carboxylic acids were also discussed. Apart from historical overview of the considered protocols, recent advances in the field were deliberated. Despite significant progress, the development of simpler, mediator-free catalytic systems based on readily available reagents remains a central challenge and a promising direction for future research.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1323-1343"},"PeriodicalIF":2.7,"publicationDate":"2026-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13635905/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149103432","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of spiro-1,2-dihydropyridine derivatives via cycloisomerization of 3-aza-1,5-enynes catalyzed by gold(I) complex/polyoxometalate hybrids. 金(I)配合物/多金属氧酸盐杂化催化3-叠氮-1,5-烯环异构化合成螺-1,2-二氢吡啶衍生物。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-28 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.106

Titien Simon, Fabian Schlimpen, Pierre de Frémont, Stefan Chassaing, Aurélien Blanc

引用次数: 0

Photochemical strategies in divalent samarium catalysis. 二价钐催化的光化学策略。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-25 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.105

Takahito Kuribara, Tetsuhiro Nemoto

引用次数: 0

Silver-catalyzed anionic [3 + 2] cycloaddition of benzyl isocyanides with polyfluoroalkylchromones and pyrones: direct synthesis of 2-arylpyrroles. 银催化苯基异氰酸酯与多氟烷基铬酮和吡咯酮的阴离子[3 + 2]环加成：2-芳基吡咯的直接合成。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-23 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.103

Ivan A Kochnev, Alexey Yu Barkov

{"title":"Silver-catalyzed anionic [3 + 2] cycloaddition of benzyl isocyanides with polyfluoroalkylchromones and pyrones: direct synthesis of 2-arylpyrroles.","authors":"Ivan A Kochnev, Alexey Yu Barkov","doi":"10.3762/bjoc.22.103","DOIUrl":"10.3762/bjoc.22.103","url":null,"abstract":"A silver-catalyzed anionic [3 + 2] cycloaddition of benzyl isocyanides has been developed, providing direct one-pot access to 2-arylpyrroles - a privileged scaffold pervasive in medicinal chemistry and functional materials. Despite high demand, general one-step routes to this motif remain rare, and the synthetic potential of benzyl isocyanides in cycloaddition chemistry has been severely limited by their low reactivity. We herein show that the combination of AgOAc (10 mol %) and KOt-Bu efficiently promote the reaction of benzyl isocyanides with 2-polyfluoroalkylchromones and 6-(trifluoromethyl)-4H-pyrones, delivering 2-arylpyrroles in yields of up to 83% with complete chemo- and regioselectivity. The protocol is operationally simple and extends readily to chromones and pyrones lacking a trifluoromethyl group, demonstrating a broad substrate scope. This work establishes a practical catalytic entry to an important heterocyclic class and unlocks the underexplored utility of benzyl isocyanides in cycloaddition reactions.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1284-1294"},"PeriodicalIF":2.7,"publicationDate":"2026-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13618341/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149073204","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

CO₂ silylation at a tucked-in iron(II) complex. 二氧化碳在铁（II）配合物中的硅基化。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-23 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.104

Logan J Taylor, Marcus W Drover

{"title":"CO2 silylation at a tucked-in iron(II) complex.","authors":"Logan J Taylor, Marcus W Drover","doi":"10.3762/bjoc.22.104","DOIUrl":"10.3762/bjoc.22.104","url":null,"abstract":"Carbon dioxide (CO2) capture and valorization remain central challenges in sustainable chemistry due to the persistence of CO2 as a major greenhouse gas. Herein, we describe the functionalization of a CO2-activated organometallic complex, [(Cp*-CO2)Fe(diphosphine)] (1; Cp* = C5Me5) in which CO2 is selectively incorporated into the Cp* ligand framework. Treatment of 1 with trimethylsilyl chloride (TMSCl) affords [{Cp*-C(O)-O-TMS}Fe(diphosphine)Cl] (2) via silylation of the Fe-O(CO2) linkage. Chloride abstraction using NaBPh4 generates the putative complex [{Cp*-C(O)-O-TMS}Fe(diphosphine)]+ (3), featuring a labile dative R2C=O→Fe interaction that is readily displaced by acetonitrile to give [{Cp*-C(O)-O-TMS}Fe(diphosphine)(NCCH3)]+ (4). Reduction of the ester functionality in 2 using HBCy2 (Cy = cyclohexyl) provides access to new borylated complexes. Collectively, these results demonstrate the cooperative capture and stepwise CO2 functionalization at a common Cp* ligand framework.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1295-1302"},"PeriodicalIF":2.7,"publicationDate":"2026-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13618351/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149073229","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Harnessing redox properties of organic persistent radicals in SET-induced transformations. 利用有机持久性自由基在set诱导转化中的氧化还原特性。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-17 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.102

Jaysan Janabel, Tynchtyk Amatov

引用次数: 0

Investigation of boron-fluorine bond reactivity in meso-aryl-substituted BODIPYs towards carborane O-nucleophiles. 介芳基取代BODIPYs对碳硼烷o亲核试剂的硼氟键反应性研究。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-09 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.100

Andrei V Zaitsev, Alexander F Smol'yakov, Victoria M Alpatova, Elena G Kononova, Anatolii Botezatu, Valentina A Ol'shevskaya

{"title":"Investigation of boron-fluorine bond reactivity in meso-aryl-substituted BODIPYs towards carborane O-nucleophiles.","authors":"Andrei V Zaitsev, Alexander F Smol'yakov, Victoria M Alpatova, Elena G Kononova, Anatolii Botezatu, Valentina A Ol'shevskaya","doi":"10.3762/bjoc.22.100","DOIUrl":"10.3762/bjoc.22.100","url":null,"abstract":"In this work meso-aryl-substituted BODIPYs (Ar = Ph, p-Br-C6H4, C6F5) were used as starting compounds for modification of their boron atoms with carborane O-nucleophiles to afford novel boron-substituted carborane BODIPY derivatives. This type of reactions has not been used previously to prepare carborane structures. The reactions proceeded via the cleavage of boron-fluorine bonds in BODIPYs under the action of AlCl3 followed by the treatment with carborane O-nucleophiles such as 1-hydroxymethyl-o-carborane or 1,2-dihydroxymethyl-o-carborane. While reactions of meso-aryl-substituted BODIPYs with 1-hydroxymethyl-o-carborane proceeded selectively, forming mono- or dicarborane-substituted BODIPYs, the reactions of 1,2-bis(hydroxymethyl)-o-carborane were not selective yielding a mixture of products. The structures of novel compounds were confirmed by 1H and 11B NMR and mass spectrometry. The structures of some prepared carborane BODIPY compounds were further supported by their single X-ray crystal structures.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1237-1245"},"PeriodicalIF":2.7,"publicationDate":"2026-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13575341/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148975714","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

A study towards the undirected fluorination and chlorination of cubane 1,4-diester. 古班1,4-二酯无定向氟化和氯化反应的研究。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-09 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.101

Laly Donnier-Valentin, Robin Heinrich, Quentin Fevre-Renault, Julien Legros, Bruno Linclau, Michaël De Paolis

引用次数: 0

Molecular structure of 3-O-acetyl-11-keto-β-boswellic acid and its ʟ-alanine conjugate (AKBA-Ala) and their impact on lipoxygenases. 3- o-乙酰-11-酮-β-乳香酸及其_ -丙氨酸偶联物（AKBA-Ala）的分子结构及其对脂氧合酶的影响。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-03 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.99

Jan M Peschel, Paul M Jordan, Benjamin Friebe, Helmar Görls, Phil Köhler, Ulrich S Schubert, Oliver Werz, Michael Gottschaldt

{"title":"Molecular structure of 3-O-acetyl-11-keto-β-boswellic acid and its ʟ-alanine conjugate (AKBA-Ala) and their impact on lipoxygenases.","authors":"Jan M Peschel, Paul M Jordan, Benjamin Friebe, Helmar Görls, Phil Köhler, Ulrich S Schubert, Oliver Werz, Michael Gottschaldt","doi":"10.3762/bjoc.22.99","DOIUrl":"10.3762/bjoc.22.99","url":null,"abstract":"3-O-Acetyl-11-keto-β-boswellic acid (AKBA) is an anti-inflammatory constituent of frankincense. Its potency is attributed to its ability to interact with enzymes in the inflammation cascade, such as lipoxygenase and cyclooxygenase, to decrease formation of pro-inflammatory products while increasing the production of pro-resolving mediators. However, the availability of AKBA in vivo may be limited by factors such as poor solubility and protein binding in serum. A prodrug approach, wherein AKBA is conjugated to amino acids through its carboxylate moiety, could be a suitable way to improve solubility and half-life in blood while maintaining anti-inflammatory efficacy. In this study, we describe a robust protocol for the preparation of high-purity amino acid-AKBA conjugates, exemplified by synthesis of the ʟ-alaninate derivative AKBA-Ala. The alanine conjugate was characterized by NMR spectroscopy, ESI-MS, HPLC, and X-ray crystallography, representing the first reported solid-state structure of an amino acid-AKBA conjugate. In comparison to AKBA, biological investigations of AKBA-Ala demonstrated a reduced inhibition (40% weaker at 10 µM) of 5-lipoxygenase (5-LOX) product formation in human neutrophils, but slightly enhanced production (120% higher at 10 µM) of specialized pro-resolving mediators (SPM) in human M2 macrophages. Overall, the anti-inflammatory potency of AKBA-Ala remains comparable to that of AKBA.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1229-1236"},"PeriodicalIF":2.7,"publicationDate":"2026-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13575334/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148975665","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Intermolecular water attack to alkenylgold carbenes derived from 3-propargylindoles. 3-丙炔啉衍生物烯基金碳烯的分子间水侵蚀。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-09-02 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.98

Lorena Renedo, Marta Solas, Samuel Suárez-Pantiga, Roberto Sanz

引用次数: 0