Beilstein Journal of Organic Chemistry最新文献_第5页

Rh(III)-catalyzed chelation-assisted C-H activation/annulation of 2-arylimidazolines with cyclic diazo-1,3-dicarbonyl compounds: a novel approach to tetracyclic annulated derivatives of 2,3-dihydroimidazo[2,1-a]isoquinoline. Rh（III）催化螯合辅助2-芳基咪唑啉与环重氮-1,3-二羰基化合物的C-H活化/环化：制备2,3-二氢咪唑[2,1-a]异喹啉四环衍生物的新方法。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-30 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.78

Ivan Lyutin, Grigory Kantin, Olga Bakulina, Dmitry Dar'in

引用次数: 0

The role of spacer length and flexibility in peptide self-assembly. 间隔段长度和灵活性在肽自组装中的作用。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-25 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.77

Julian Link, Albin Lahu, Manfred Wagner, Tanja Weil, David Y W Ng

引用次数: 0

Novel macrocycles: from synthesis to supramolecular function. 新型大环：从合成到超分子功能。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-24 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.76

Veronica Iuliano, Carmen Talotta, Margherita De Rosa, Paolo Della Sala, Konrad Tiefenbacher, Pablo Ballester, Carmine Gaeta

引用次数: 0

Electrochemical reduction of unsaturated carbon-carbon bonds via 3d transition-metal catalysis. 通过三维过渡金属催化的电化学还原不饱和碳-碳键。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-17 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.75

Geon Kang, Minki Jeon, Pooja Kumari Jat, Cheoljae Kim, Isaac Choi

引用次数: 0

Synthesis of sterically shielded piperidine nitroxides via acid-catalyzed heterocyclization of β-aminoketone derivatives with ketones. 酸催化β-氨基酮衍生物与酮的杂环化合成立体屏蔽哌啶类氮氧化物。

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2026-06-17 eCollection Date: 2026-01-01 DOI: 10.3762/bjoc.22.74

Mark M Gulman, Yurii I Glazachev, Sergey A Dobrynin

{"title":"Synthesis of sterically shielded piperidine nitroxides via acid-catalyzed heterocyclization of β-aminoketone derivatives with ketones.","authors":"Mark M Gulman, Yurii I Glazachev, Sergey A Dobrynin","doi":"10.3762/bjoc.22.74","DOIUrl":"10.3762/bjoc.22.74","url":null,"abstract":"The capabilities of modern methods for the synthesis of sterically shielded piperidine nitroxides with acyclic substituents are largely limited to symmetrical tetraethyl structures and do not allow the introduction of functional groups into position 2. We propose an alternative approach that allows for the variation of substituents adjacent to the nitroxyl group, which significantly expands the potential of sterically hindered nitroxides for promising applications in materials science and structural biology. The new heterocyclization strategy implies the construction of a 2,2,6-trisubstituted piperidine scaffold from β-aminoketone acetals and dialkyl ketones under acid catalysis. The resulting amines were oxidized to the corresponding ketonitrones and subsequent reaction with moderately basic organometallic reagents, such as 2-alkynyl- and 2-allylmagnesium halides, enables the facile introduction of diverse substituents, including those with functional groups. If necessary, the multiple carbon-carbon bonds in the side chain can be subjected to hydrogenation to give saturated alkyl or functionalized alkyl groups. The study of reduction kinetics for alkyl and allyl-substituted piperidine nitroxides in ascorbate/glutathione media (30% EtOH, pH 7.5) yielded second-order rate constants of ≈10-2 M-1·s-1, which is close to that earlier reported for 2,2,6,6-tetraethylpiperidine (TEEPONE).","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"948-954"},"PeriodicalIF":2.7,"publicationDate":"2026-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13284749/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148306585","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

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