Beilstein Journal of Organic Chemistry最新文献_第3页

Recent advances in copper-catalyzed direct hydroamination of alkenes with (hetero)aromatic amines. 铜催化烯烃与（杂）芳胺直接氢胺化反应的研究进展。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-11 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.73

Hyejeong Lee, Yunmi Lee

{"title":"Recent advances in copper-catalyzed direct hydroamination of alkenes with (hetero)aromatic amines.","authors":"Hyejeong Lee, Yunmi Lee","doi":"10.3762/bjoc.22.73","DOIUrl":"10.3762/bjoc.22.73","url":null,"abstract":"Nitrogen-containing aromatic amines and aza-heterocycles are ubiquitous motifs in pharmaceuticals and functional materials, making efficient C-N bond formation a fundamental transformation in synthetic chemistry. The direct hydroamination of alkenes using (hetero)aromatic N-H nucleophiles offers an atom- and step-economical strategy; however, the reduced nucleophilicity and distinct coordination behavior of these substrates render such transformations inherently challenging. Recently, copper catalysis has emerged as a versatile and practical platform for addressing these limitations. Owing to its redox flexibility and ligand tunability, copper facilitates multiple activation modes, including copper-amido-mediated nucleophilic addition or aminocupration, Lewis acid-type alkene activation, and radical-mediated pathways. These complementary mechanisms provide access to diverse alkene classes with control over regioselectivity (Markovnikov vs anti-Markovnikov addition), stereoselectivity, and functional group tolerance. This review summarizes recent advances in the copper-catalyzed hydroamination of alkenes with (hetero)aromatic N-H nucleophiles, emphasizing the mechanistic paradigms and the factors governing selectivity.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"925-947"},"PeriodicalIF":2.7,"publicationDate":"2026-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13267513/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148263096","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 practical CO₂-mediated synthesis of 5,6-carboxylated silicon-rhodamines for targeted probe development. 用于靶向探针开发的5,6-羧基化硅罗丹明的co2介导合成。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-10 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.72

Dongjie Hou, Shaowei Wu, Ning Xu, Pengjun Bao, Wenhao Jia, Qinglong Qiao, Zhaochao Xu

{"title":"A practical CO2-mediated synthesis of 5,6-carboxylated silicon-rhodamines for targeted probe development.","authors":"Dongjie Hou, Shaowei Wu, Ning Xu, Pengjun Bao, Wenhao Jia, Qinglong Qiao, Zhaochao Xu","doi":"10.3762/bjoc.22.72","DOIUrl":"10.3762/bjoc.22.72","url":null,"abstract":"Silicon-rhodamine (SiR) dyes are among the most important fluorophores for super-resolution imaging owing to their far-red emission, high photostability, and tunable lactone-zwitterion equilibrium. However, their broader application in targeted probe development has been limited by the challenging synthesis of 5,6-carboxylated SiR derivatives, which are essential intermediates for bioconjugation. Here, we report a practical CO2-mediated strategy for the synthesis of 5,6-carboxylated SiRs from brominated SiR precursors via lithium-halogen exchange and direct carboxylation. Using n-BuLi and readily available CO2, this method delivers carboxylated SiR derivatives in 60-93% yields while avoiding the use of t-BuLi, toxic CO, and expensive palladium catalysts. In addition, the crude carboxylation mixtures can be directly subjected to amide coupling without chromatographic purification, enabling one-pot access to HaloTag-targeted SiR probes. The resulting probes were successfully applied to long-term live-cell super-resolution imaging, allowing visualization of filopodial dynamics and mitochondrial remodeling. This work establishes a concise and efficient route to functionalized SiR dyes and facilitates the rapid development of targeted SiR probes.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"915-924"},"PeriodicalIF":2.7,"publicationDate":"2026-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13267498/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148263084","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

Cascade transformation of 2-(diazoacetyl)-2H-azirines to 2-aroyl-3-hydroxy-1H-pyrroles via condensation with aromatic aldehydes. 2-（重氮乙酰基）- 2h -氮嘧啶通过与芳香醛缩合而级联转化为2-芳基-3-羟基- 1h -吡咯。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-09 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.70

Timur O Zanakhov, Ekaterina E Galenko, Mikhail S Novikov, Alexander F Khlebnikov

引用次数: 0

Palladium-catalyzed benzocyclization reactions of quinoline-2-carboxamides via sequential C-H/N-H functionalization. 钯催化喹啉-2-羧基酰胺序贯C-H/N-H功能化的苯并环化反应。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-09 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.71

Shoichi Sugita, Kentaro Okano, Atsunori Mori

{"title":"Palladium-catalyzed benzocyclization reactions of quinoline-2-carboxamides via sequential C-H/N-H functionalization.","authors":"Shoichi Sugita, Kentaro Okano, Atsunori Mori","doi":"10.3762/bjoc.22.71","DOIUrl":"10.3762/bjoc.22.71","url":null,"abstract":"A novel benzocyclization protocol has been developed for the synthesis of quinoline-fused lactams by palladium-catalyzed sequential C-H/N-H functionalization of quinoline-2-carboxamides and 1,2-dihaloarenes. The reaction proceeds at the C-H bond on the quinoline adjacent to the amide group and at the amide N-H bond in the presence of 10 mol % Pd(OAc)2 in o-xylene as a solvent to afford the cyclized product in 34% yield. The yield increases to 81% when the reaction is carried out with 80 mol % P(4-MeOC6H4)3 as a ligand and with an increased catalyst loading of 20 mol %. The reaction affords lactams in up to 83% yield using amides containing various functional groups and substituted 1-bromo-2-iodobenzenes. Furthermore, 1,2-dibromo heteroarenes, such as benzothiophene and pyridine, undergo annulation to give the corresponding heterocycle-fused compounds. The high chemoselectivity of the 1,2-dihaloarene functional groups is confirmed in this reaction, thus enabling divergent synthesis of various multifused heterocyclic systems.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"905-914"},"PeriodicalIF":2.7,"publicationDate":"2026-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13267496/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148263017","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

Chiral cyclopropenimine-catalyzed enantioselective Michael reactions of phenol and benzofuran-derived α,β-unsaturated pyrazolamides with benzophenone-imine of glycine esters. 手性环丙烯胺催化苯酚和苯并呋喃衍生的α，β-不饱和吡唑酰胺与二苯甲酮-亚胺甘氨酸酯的对映选择性Michael反应。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-08 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.69

Ya Bai, Xue-Ying Wang, Si-Kai Zhu, Yan-Ting Shen, Sheng-Yong Zhang, Ping-An Wang

引用次数: 0

Diastereodivergent electrophilic trapping of α-boryl lithium derivatives. α-硼基锂衍生物的非对映发散亲电俘获。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-05 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.68

Tereza Pavlíčková, Noam Orbach, Ilan Marek

{"title":"Diastereodivergent electrophilic trapping of α-boryl lithium derivatives.","authors":"Tereza Pavlíčková, Noam Orbach, Ilan Marek","doi":"10.3762/bjoc.22.68","DOIUrl":"10.3762/bjoc.22.68","url":null,"abstract":"α-Boryl carbanions are valuable organoboron intermediates, but controlling their stereoselective reactions remains challenging. Here, we examine the diastereoselective generation and trapping of α-boryl lithium species formed by ring opening of substituted iodomethylcyclopropanes. After lithium-iodine exchange and selective C-C bond cleavage, these intermediates react with a range of electrophiles to give boronic esters bearing vicinal tri- and tetrasubstituted stereocenters in good yields and high diastereoselectivities. Notably, substrates bearing alkyl substituents display the opposite sense of diastereoselectivity to previously studied aryl-substituted analogues. The results suggest that the stereochemical outcome is independent of the initial configuration at C2 and is instead dictated by conformational preferences of the α-boryl lithium intermediate. A simplified steric model is proposed in which lithium coordination induces a pseudo-chelated structure that controls facial selectivity during electrophilic trapping. These findings expand the synthetic utility of α-boryl lithium intermediates and provide insight into the origins of their diastereoselectivity.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"882-887"},"PeriodicalIF":2.7,"publicationDate":"2026-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13245471/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148209773","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

Site-specific labelling of native peptides and proteins: chemical and enzymatic strategies. 位点特异性标记的天然肽和蛋白质：化学和酶的策略。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-03 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.67

Antonio Angelastro, Jonathan Bargh, Subhajit Guria, Victor Laserna, Louis Luk

引用次数: 0

Unsymmetrical sulfoxides with sterically hindered catechol fragment: synthesis, structure, electrochemical properties, and antiradical activity. 具有位阻儿茶酚片段的不对称亚砜：合成、结构、电化学性质和抗自由基活性。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-01 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.65

Daria A Burmistrova, Vasiliy A Fokin, Oleg P Demidov, Mikhail A Kiskin, Maxim V Arsenyev, Andrey I Poddel'sky, Nadezhda T Berberova, Ivan V Smolyaninov

{"title":"Unsymmetrical sulfoxides with sterically hindered catechol fragment: synthesis, structure, electrochemical properties, and antiradical activity.","authors":"Daria A Burmistrova, Vasiliy A Fokin, Oleg P Demidov, Mikhail A Kiskin, Maxim V Arsenyev, Andrey I Poddel'sky, Nadezhda T Berberova, Ivan V Smolyaninov","doi":"10.3762/bjoc.22.65","DOIUrl":"10.3762/bjoc.22.65","url":null,"abstract":"New unsymmetrical sulfoxides containing a redox-active sterically hindered catechol fragment and a nonpolar hydrocarbon substituent at the sulfoxide group were synthesized via the oxidation of the corresponding catechol thioethers with hydrogen peroxide. The yield of the reaction products ranges from 42 to 89%. The crystal structures of catechol sulfoxides with isopropyl, cyclopentyl, adamantyl, benzyl and 1-naphthyl moieties were established by single-crystal X-ray analysis. The possibility of forming intra- and intermolecular hydrogen bonds has been shown for these compounds. The electrochemical behavior of sulfoxides was studied in comparison with that of the parent catechol thioethers. The redox transition corresponding to catechol fragment oxidation is shifted to the anodic region relative to the initial thioethers, which is attributed to the more electron-withdrawing nature of the S=O group. The second redox stage characterizes the transformation of the sulfoxide fragment and is observed in most cases at 1.82-1.91 V. The radical-scavenging activity and antioxidant properties of the unsymmetrical sulfoxides and their precursor thioethers were evaluated using the reaction with the 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) and the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS+•). In both assays, the lowest IC50 values among the studied catechol sulfoxides were found for compounds bearing isopropyl and tert-butyl substituents on the sulfoxide group.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"828-837"},"PeriodicalIF":2.7,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13245472/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148209702","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

The trans-influence in gold chemistry from a catalytic perspective. 从催化的角度看对金化学的影响。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-01 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.66

Manfred Bochmann

引用次数: 0

Total synthesis of the capsular polysaccharide repeating unit towards the development of a glycoconjugate vaccine against Klebsiella pneumoniae ST512. 荚膜多糖重复单元的全合成及其对肺炎克雷伯菌ST512糖结合疫苗的研制

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-05-29 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.64

Shuo Zhang, Ondřej Daněk, Peter H Seeberger

引用次数: 0