Advanced Synthesis & Catalysis最新文献

Thiolane Sulfoximines as Azide Surrogates for Quinolyl Nitrenes: Photochemical Access to Ortho ‐Diaminoquinolines 噻吩亚砜亚胺作为喹酰亚胺叠氮化物的替代物：邻二氨基喹啉的光化学途径

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-19 DOI: 10.1002/adsc.70813

Lorenzo Serusi, Timothé Maujean, Camille Van Wesemael, Romain Pertschi, Vicenç Branchadell, Mihaela Gulea

{"title":"Thiolane Sulfoximines as Azide Surrogates for Quinolyl Nitrenes: Photochemical Access to Ortho ‐Diaminoquinolines","authors":"Lorenzo Serusi, Timothé Maujean, Camille Van Wesemael, Romain Pertschi, Vicenç Branchadell, Mihaela Gulea","doi":"10.1002/adsc.70813","DOIUrl":"https://doi.org/10.1002/adsc.70813","url":null,"abstract":"Quinolyl nitrenes are valuable reactive intermediates for the synthesis of nitrogen‐containing heterocycles but are commonly generated from hazardous azides under photochemical conditions. Herein, we introduce quinolyl thiolane sulfoximines as practical and thermally stable precursors for the photochemical generation of 8‐quinolyl nitrenes. Upon UV irradiation, these sulfoximines undergo selective S─N bond cleavage and react efficiently with primary and secondary amines, providing direct access to structurally diverse 7,8‐diaminoquinolines in moderate to excellent yields. The transformation releases tetramethylene S‐oxide as a small, benign, readily removable by‐product and exhibits broad functional‐group tolerance, including compatibility with amino acid derivatives, enabling the synthesis of valuable fused δ‐lactam scaffolds. DFT calculations support a mechanism involving nitrene formation followed by azirine trapping and rationalize the experimentally observed selectivity between diaminoquinoline and aminoazepine products. Overall, this work establishes quinolyl sulfoximines as practical and safer surrogates for azides in nitrene photochemistry, providing an efficient platform for the synthesis of 7,8‐diaminoquinolines.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"56 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218739","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Ciprofloxacin Hydrochloride‐Enhanced Potassium tert ‐Butoxide‐Mediated Direct Pyrazinylation of (Hetero)aryl Halides 盐酸环丙沙星-增强叔丁醇钾-介导的（杂）芳基卤化物直接吡嗪化

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-19 DOI: 10.1002/adsc.70832

Dake Song, Haijie Yang, Zhen Zhang, Yawen Hu, Yi Qin, Changxu Zhao, Ying Liu, Jifan Wang, Xuefei Bao, Guoliang Chen

{"title":"Ciprofloxacin Hydrochloride‐Enhanced Potassium tert ‐Butoxide‐Mediated Direct Pyrazinylation of (Hetero)aryl Halides","authors":"Dake Song, Haijie Yang, Zhen Zhang, Yawen Hu, Yi Qin, Changxu Zhao, Ying Liu, Jifan Wang, Xuefei Bao, Guoliang Chen","doi":"10.1002/adsc.70832","DOIUrl":"https://doi.org/10.1002/adsc.70832","url":null,"abstract":"Aryl pyrazines are increasingly prevalent in the fields of pharmaceuticals and luminescent materials. Base‐promoted cross‐coupling reactions of (hetero)aryl halides with pyrazines can effectively avoid the drawbacks of limited substrate sources in conventional condensation and the cost as well as toxicity issues of noble metal catalysts inherent in transition metal‐catalyzed methods. However, existing methods are predominantly applicable to (hetero)aryl iodides and bromides, whereas the direct use of less reactive (hetero)aryl chlorides remains challenging. Herein, we report a ciprofloxacin hydrochloride with potassium tert ‐butoxide ( t ‐BuOK) catalytic system for the construction of aryl pyrazines. In this reaction, a variety of (hetero)aryl bromides and chlorides prove to be viable substrates and exhibit excellent compatibility with a variety of functional groups. The developed system allows the preparation of aryl pyrazines on a gram‐scale and the functionalization of complex pharmaceuticals. Mechanistic studies reveal that a radical‐mediated pathway is involved in this catalytic transformation.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"65 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218740","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Chemoselective Recognition of Vinyl Organometalloids in Cobalt‐Catalyzed Hydrosilylation 乙烯基类有机金属在钴催化硅氢化反应中的化学选择性识别

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-19 DOI: 10.1002/adsc.70824

Hanna Stachowiak‐Dłużyńska, Miłosz Makowski, Agnieszka M. Janiak, Grzegorz Hreczycho

引用次数: 0

Late‐Stage Diversification of Carbazolyl‐Derived Phosphines via Ru(II)‐Catalyzed P(III)‐Directed C─H Alkenylation With Internal Alkynes Ru（II）催化P（III）导向C─H烯化与内炔的后期多样化咔唑基衍生膦

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-19 DOI: 10.1002/adsc.70828

Tiantian Zhu, Xuecong Huang, Yongru He, Fengling Zhou, Taoyuan Liang, Shuangliang Zhao, Zhuan Zhang

引用次数: 0

Regioselective Diversification of Aminopyrazoles via Ir‐Catalyzed C─H Borylation 通过Ir催化的C─H硼化反应氨基吡唑的区域选择性多样化

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-19 DOI: 10.1002/adsc.70689

Jay S. Wright, Felipe M. Nogueira, Andrew C. Hones, Mingyan Ding, Mark A. Fox, Wender A. Silva, Angelo H. de Lira Machado, Alpay Dermenci, David C. Blakemore, Patrick G. Steel

引用次数: 0

Visible‐Light‐Triggered Hydroacylation of α ‐Imino Esters With α ‐Keto Esters via Substrate Self‐Catalysis 通过底物自催化，可见光触发α -亚胺酯与α -酮酯的氢化反应

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-19 DOI: 10.1002/adsc.70831

Xiaoling Cheng, Xianda Wu, Zeen Chen, Lin Shen, Lei Gong, Yu‐Mei Lin

{"title":"Visible‐Light‐Triggered Hydroacylation of α ‐Imino Esters With α ‐Keto Esters via Substrate Self‐Catalysis","authors":"Xiaoling Cheng, Xianda Wu, Zeen Chen, Lin Shen, Lei Gong, Yu‐Mei Lin","doi":"10.1002/adsc.70831","DOIUrl":"https://doi.org/10.1002/adsc.70831","url":null,"abstract":"α ‐Ketoamides are important structural motifs in bioactive molecules. While conceptually efficient, direct acylation of imines toward α ‐ketoamides is hindered by their intrinsic instability and reactivity challenges. Here, we disclose a photochemical hydroacylation of α ‐imino esters with α ‐keto esters that operates without any transition metal or external photosensitizer. Mechanistic elucidation reveals that the α ‐keto ester plays a triple role: It serves as an unconventional hydroacylation donor, a visible‐light absorber, and a hydrogen‐atom abstractor, collectively enabling substrate‐driven self‐catalysis. This strategy provides rapid access to structurally diverse α ‐ketoamide derivatives (44 examples) with high yields (up to 97%) under mild, environmentally benign conditions. By integrating multifunctional substrates and self‐catalytic photoreactivity, this approach expands the toolbox for constructing complex ketoacyl frameworks, offering a concise route toward pharmaceutically relevant motifs.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218693","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of γ , γ ‐Disubstituted γ ‐Butyrolactones via Copper‐Catalyzed Arylation–Lactonization of γ ,δ‐Unsaturated Esters With Diaryliodonium Salts 铜催化γ，δ -不饱和酯与二芳基碘鎓盐芳基内酯化合成γ， γ‐二取代γ‐丁内酯

IF 5.4 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-19 DOI: 10.1002/adsc.70821

Kosuke Yamamoto, Iori Ohmae, Harutaka Toyomaru, Sora Hirose, Yosuke Demizu, Masami Kuriyama, Osamu Onomura

引用次数: 0

Ball-Milling-Enabled Solvent- and Ligand-Free Tsuji–Trost Reaction of C-, N-, O-, S-, and Se-Nucleophiles in Air: Synthesis and Late-Stage Modification of Drugs 空气中C-、N-、O-、S-和se -亲核试剂的无溶剂和无配体球磨反应：药物的合成和后期修饰

IF 3.7 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-15 DOI: 10.1002/adsc.70811

Keya Roy, Anay Saha, Himadry Mandal, Somnath Giri, Bijay Saha, Sumanta Kumar Sahu, Laksmikanta Adak

{"title":"Ball-Milling-Enabled Solvent- and Ligand-Free Tsuji–Trost Reaction of C-, N-, O-, S-, and Se-Nucleophiles in Air: Synthesis and Late-Stage Modification of Drugs","authors":"Keya Roy, Anay Saha, Himadry Mandal, Somnath Giri, Bijay Saha, Sumanta Kumar Sahu, Laksmikanta Adak","doi":"10.1002/adsc.70811","DOIUrl":"10.1002/adsc.70811","url":null,"abstract":"We report a novel ball-milling-enabled, ligand-free Tsuji–Trost reaction involving C-, N-, O-, S-, and Se-nucleophiles with allyl and cinnamyl acetates, as well as allyl phosphate. Thiophenols and benzeneselenol have been demonstrated for the first time as nucleophiles in a ball-milling-assisted Tsuji–Trost reaction. The reaction proceeds at room temperature under air without the need for a solvent, and exhibits a broad substrate scope (41 examples). In addition, this study successfully establishes the unexplored mechanochemical synthesis of a series of commercially available drugs containing allyl functional groups, as well as the late-stage modification of several marketed drugs, highlighting the potential of this method in pharmaceutical applications and drug discovery. The practical utility of this methodology is further demonstrated through a gram-scale reaction of the Cinnarizine drug, followed by downstream derivatization and reusability of the catalyst. Additionally, several spectroscopic experiments have been conducted for the first time to gain mechanistic insight and elucidate the proposed catalytic cycle of the Tsuji–Trost reaction under ball-milling conditions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"368 21","pages":""},"PeriodicalIF":3.7,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173118","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Allylation of (Hetero)aryl Thioethers and Related Compounds With 2-Alkenylaziridines （杂）芳基硫醚及相关化合物与2-烯肯二嗪的烯丙基化

IF 3.7 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-15 DOI: 10.1002/adsc.70827

Jing-Jing Nie, Zhong-Xia Wang

引用次数: 0

Sulfide-Ene Reactions by Visible-Light-Mediated Phosphine Redox Catalysis 可见光介导的膦氧化还原催化硫化物-烯反应

IF 3.7 2区化学

Advanced Synthesis & Catalysis Pub Date : 2026-10-15 DOI: 10.1002/adsc.70805

Yingdi Wen, Jie Wang, Jie Zhang, Yunbo Zhu

{"title":"Sulfide-Ene Reactions by Visible-Light-Mediated Phosphine Redox Catalysis","authors":"Yingdi Wen, Jie Wang, Jie Zhang, Yunbo Zhu","doi":"10.1002/adsc.70805","DOIUrl":"10.1002/adsc.70805","url":null,"abstract":"Sulfur-containing compounds play a crucial role in many biological processes. The important gasotransmitter hydrogen sulfide (H2S) can be metabolized by cellular enzyme system for the biosynthesis of amino acids and regulatory effects related to diseases. Although the photocatalytic thiol-ene reactions have been widely developed, a general H2S-ene reaction by organic photocatalysis remains elusive. Inspired by enzyme-catalyzed SN2 dialkylation, we report a visible-light-mediated H2S-ene radical dialkylation by phosphine redox catalysis. This challenge is addressed by the mechanism of photoexcited P(III)–P(V) cation-catalyzed thiyl radical addition to alkenes. The H2S can be readily incorporated into a wide range of alkenes to access complex high-value-added sulfur-containing scaffolds, especially the late-stage functionalization of the alkenes derived from drugs and the cascade cyclization of dienes. This mild method also performs very well in the thiol-ene reactions, which are further applied to the synthesis of unsymmetric thioethers, macrocyclic sulfides, the conjugation of biomolecules, and sulfur-containing drugs. This strategy holds significant promise in the bioconjugation and the discovery of bioactive organosulfur compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"368 21","pages":""},"PeriodicalIF":3.7,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149173116","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0