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Thiocarbonyl‐Directed Iridium‐Catalyzed C−H Silylation of Indoles and Pyrroles with Hydrosilanes 硫代羰基引导的铱催化吲哚和吡咯与氢硅烷的 C-H 硅烷化反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202400903
Yi Cheng , Jingyi Zhan , Lei Wang , Houyun Teng , Li‐Wen Xu , Lei Yang
{"title":"Thiocarbonyl‐Directed Iridium‐Catalyzed C−H Silylation of Indoles and Pyrroles with Hydrosilanes","authors":"Yi Cheng ,&nbsp;Jingyi Zhan ,&nbsp;Lei Wang ,&nbsp;Houyun Teng ,&nbsp;Li‐Wen Xu ,&nbsp;Lei Yang","doi":"10.1002/adsc.202400903","DOIUrl":"10.1002/adsc.202400903","url":null,"abstract":"<div><div>Herein, hydrogen‐acceptor‐free C2‐selective iridium‐catalyzed C−H silylation of indoles and pyrroles with hydrosilanes via C(<em>sp</em><sup>2</sup>)−H bond activation to generate the desired silylated products is presented. The developed protocol allows for the C−H silylation of a wide range of functionalized indoles with monohydrosilanes under iridium catalysis. Significantly, this process represents a rare silylation of C−H bonds using <em>S</em>‐directing groups.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202400903"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142317722","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 Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles 邻炔基芳酰胺的化学选择性氧化钯化反应触发位点选择性 C-H 嵌合以立体选择性合成丁二酰亚胺融合多环化合物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202301367
Dattatri , Jagadeesh Babu Nanubolu , Maddi Sridhar Reddy
{"title":"Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles","authors":"Dattatri ,&nbsp;Jagadeesh Babu Nanubolu ,&nbsp;Maddi Sridhar Reddy","doi":"10.1002/adsc.202301367","DOIUrl":"10.1002/adsc.202301367","url":null,"abstract":"<div><div>We report herein a palladium‐catalyzed, site‐selective cyclative annulation of <em>o</em>‐alkynyl arylamides with maleimide for the stereoselective construction of succinimide‐fused benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, and downstream transformations. Control and labeling experiments were conducted to get insights into the mechanism.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202301367"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140164983","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
Chemo‐/Regioselective [5+1] Annulation with gem‐Difluoromethylene Allenes for the Assembly of Fluorinated 2H‐Chromenes and Dihydroquinolines 化学/区域选择性[5+1]环化宝石-二氟亚甲基烯组装氟化2h -铬和二氢喹啉
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401110
Zhensheng Lin , Ying Cai , Junwei Ye , Kaifeng Chen , Jieni Zheng , Linxin Zhou , Zhi Zhou , Wei Yi
{"title":"Chemo‐/Regioselective [5+1] Annulation with gem‐Difluoromethylene Allenes for the Assembly of Fluorinated 2H‐Chromenes and Dihydroquinolines","authors":"Zhensheng Lin ,&nbsp;Ying Cai ,&nbsp;Junwei Ye ,&nbsp;Kaifeng Chen ,&nbsp;Jieni Zheng ,&nbsp;Linxin Zhou ,&nbsp;Zhi Zhou ,&nbsp;Wei Yi","doi":"10.1002/adsc.202401110","DOIUrl":"10.1002/adsc.202401110","url":null,"abstract":"<div><div>A variety of fluorinated 2<em>H</em>‐chromenes and dihydroquinolines was synthesized by virtue of <em>gem</em>‐difluoromethylene allenes as versatile coupling partners to participate in the transition metal‐catalysed cascade C−H activation/[5+1] annulation of 2‐alkenylphenols/anilines. This protocol features specific chemo‐/regioselectivity, redox‐neutral manner and good compatibility, providing a straightforward synthetic route to intriguing motifs with the equipment of attractive fluoroalkenyl moiety. The distinctive <em>gem</em>‐difluorine effect induced an unexpected protonolysis of σ carbon‐metal bond, thus accounting for the observed selectivity via sequential C−H activation/allene insertion/protonolysis/cyclization/β‐F elimination process.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401110"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142763628","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
Regioselective Cobalt‐Catalyzed Protoboration of Alkynes 区域选择性钴催化炔的原硼化反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401334
Ho Seong Hwang , Eun Jin Cho
{"title":"Regioselective Cobalt‐Catalyzed Protoboration of Alkynes","authors":"Ho Seong Hwang ,&nbsp;Eun Jin Cho","doi":"10.1002/adsc.202401334","DOIUrl":"10.1002/adsc.202401334","url":null,"abstract":"<div><div>A regioselective cobalt‐catalyzed protoboration of alkynes has been developed, utilizing diboron as the borylation source for the efficient synthesis of alkenylborates. The reaction proceeds via cobalt‐boryl intermediates, diverging from conventional Co−H chemistry. By fine‐tuning the phosphine ligand side chains, we achieved excellent reactivity and regioselectivity across a wide range of internal and terminal alkynes. This Co‐catalyzed method offers significant advantages in terms of both efficiency and environmental impact, making it an attractive approach for the synthesis of complex organic molecules.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401334"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142782814","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
From gem‐Dichlorocyclobutenones to Cyclobutenols: Unveiling a Ruthenium‐Catalyzed Allylic Reduction‐Asymmetric Transfer Hydrogenation Cascade 从二氯环丁烯酮到环丁烯醇：揭示钌催化的烯丙基还原-不对称转移氢化级联反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401406
Olivier Charron , Marharyta Kosiuha , Virginie Ratovelomanana‐Vidal , Phannarath Phansavath , Geoffrey Gontard , Christophe Meyer
{"title":"From gem‐Dichlorocyclobutenones to Cyclobutenols: Unveiling a Ruthenium‐Catalyzed Allylic Reduction‐Asymmetric Transfer Hydrogenation Cascade","authors":"Olivier Charron ,&nbsp;Marharyta Kosiuha ,&nbsp;Virginie Ratovelomanana‐Vidal ,&nbsp;Phannarath Phansavath ,&nbsp;Geoffrey Gontard ,&nbsp;Christophe Meyer","doi":"10.1002/adsc.202401406","DOIUrl":"10.1002/adsc.202401406","url":null,"abstract":"<div><div>Cyclobutenones constitute an appealing class of substrates in catalytic asymmetric transformations leading to diversely substituted enantioenriched four‐membered carbocycles, which are eliciting a growing interest in medicinal chemistry. Whilst several synthetically useful enantioselective conjugate addition reactions have been reported, the catalytic enantioselective reduction of the carbonyl group of simple cyclobutenones remains an elusive transformation. Herein, we disclose the discovery of a novel allylic reduction‐asymmetric transfer hydrogenation cascade, catalyzed by a Noyori‐Ikariya ruthenium complex, from readily available <em>gem</em>‐dichlorocyclobutenones, leading to 2‐chlorocyclobutenols with high optical purities, which can be engaged in postfunctionalization reactions enabling access to substituted four‐membered rings.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401406"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202401406","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142735823","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Vinyl Sulfones and Benzoxathiins via Base‐Catalyzed Reactions of o‐Hydroxyaryl Thiosulfonates and Ynones 通过邻羟基芳基硫代磺酸盐和炔酮的碱催化反应合成乙烯基砜和苯并氧硫杂环胺
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202400456
Delin Tang , Fang Zhang , Jinyun Luo , Zhihua Cai , Lin He , Guangfen Du
{"title":"Synthesis of Vinyl Sulfones and Benzoxathiins via Base‐Catalyzed Reactions of o‐Hydroxyaryl Thiosulfonates and Ynones","authors":"Delin Tang ,&nbsp;Fang Zhang ,&nbsp;Jinyun Luo ,&nbsp;Zhihua Cai ,&nbsp;Lin He ,&nbsp;Guangfen Du","doi":"10.1002/adsc.202400456","DOIUrl":"10.1002/adsc.202400456","url":null,"abstract":"<div><div>The cyclization reaction and hydrosulfonylation reaction of ynones have been simultaneously realized through a single operation. Under the mediation of cesium carbonate, different <em>S</em>‐(<em>α</em>‐hydroxyaryl) aryl thiosulfonates reacted with various ynones to produce functionalized vinyl sulfones in 37%–83% yields with <em>E</em>‐selectivity. At the same time, a variety of benzoxathiins were formed in 42%–97% yields.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202400456"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374469","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 Tetrahydro‐β‐carbolines via Cascade Sigmatropic Rearrangements 通过级联西格玛式重排合成四氢-β-羰基化合物
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401189
Daiki Oka , Tomomi Ohtsuka , Ken‐ichi Takao , Akihiro Ogura
{"title":"Synthesis of Tetrahydro‐β‐carbolines via Cascade Sigmatropic Rearrangements","authors":"Daiki Oka ,&nbsp;Tomomi Ohtsuka ,&nbsp;Ken‐ichi Takao ,&nbsp;Akihiro Ogura","doi":"10.1002/adsc.202401189","DOIUrl":"10.1002/adsc.202401189","url":null,"abstract":"<div><div>We have developed a synthesis for tetrahydro‐β‐carbolines involving cascade sigmatropic rearrangements. The substrates were conveniently prepared from parent anilines via a [2,3]‐sigmatropic rearrangement and cyanomethylation. Silver‐mediated decyanation afforded the corresponding iminium cation, which underwent a cascade consisting of an aza‐Cope rearrangement, an aza‐oxa‐Cope rearrangement, an aromatization, and a Pictet‐Spengler reaction, and tetrahydro‐β‐carbolines were obtained as the single product. The reaction involved seven bond scissions and four bond formations and was triggered by a single reagent.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401189"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202401189","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609892","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Pd‐Catalyzed Denitrative C2‐Arylation of Oxazoles, Benzoxazoles, and Benzimidazoles with Nitroarenes pd催化恶唑、苯并恶唑和苯并咪唑与硝基芳烃的c2 -芳基化反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401332
Lin Feng , Haiyan Li , Lei Huang , Jiaxin Yao , Wengui Duan , Lin Yu
{"title":"Pd‐Catalyzed Denitrative C2‐Arylation of Oxazoles, Benzoxazoles, and Benzimidazoles with Nitroarenes","authors":"Lin Feng ,&nbsp;Haiyan Li ,&nbsp;Lei Huang ,&nbsp;Jiaxin Yao ,&nbsp;Wengui Duan ,&nbsp;Lin Yu","doi":"10.1002/adsc.202401332","DOIUrl":"10.1002/adsc.202401332","url":null,"abstract":"<div><div>A step‐economic method for C2‐arylated azoles via Pd‐catalyzed denitrative arylation of nitroarenes and azoles is reported. This protocol employs synthetically upstream nitroarenes as arylating reagents and proceeds through the selective cleavage of the C−NO<sub>2</sub> and C−H bonds. Various nitroarenes and nitroheteroarenes were coupled with oxazoles, benzoxazoles, and methylbenzimidazoles, achieving yields of up to 95%. The method's utility is exemplified by its application in the synthesis of Flunoxaprofen. This strategy reduces synthetic steps and minimizes pollution, offering substantial cost‐effectiveness and environmental benefits. Furthermore, the relatively inert C−NO<sub>2</sub> bond in nitroarenes enables late‐stage functionalization or stepwise coupling reactions, providing a complementary method for C2‐arylation of azoles.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401332"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753420","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
Base‐Promoted [4+3] Cycloadditions of N‐Thioacylimines with α‐Chlorohydroxamates: Construction of 1,3,5‐Thiadiazepin‐6(7H)‐One Derivatives n-硫酰基与α-氯羟酸酯的碱促进[4+3]环加成：1,3,5-噻二氮平-6(7H)- 1衍生物的构建
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401193
Yu‐Di Liu , Yu‐Heng Shao , Zhao‐Lin He , Gang Wang
{"title":"Base‐Promoted [4+3] Cycloadditions of N‐Thioacylimines with α‐Chlorohydroxamates: Construction of 1,3,5‐Thiadiazepin‐6(7H)‐One Derivatives","authors":"Yu‐Di Liu ,&nbsp;Yu‐Heng Shao ,&nbsp;Zhao‐Lin He ,&nbsp;Gang Wang","doi":"10.1002/adsc.202401193","DOIUrl":"10.1002/adsc.202401193","url":null,"abstract":"<div><div>A metal‐free base‐promoted [4+3] cycloaddition reaction of <em>N</em>‐thioacyl imines in situ generated from α‐amido sulfones with α‐chlorohydroxamates is described. The reaction allows the straightforward synthesis of 1,3,5‐thiadiazepin‐6(7<em>H</em>)‐one derivatives in 44~90% yields. Moreover, a gram‐scale reaction and a product transformation were conducted, which further increased the diversity of products.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401193"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142753428","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
DMSO/SOCl2‐Mediated Synthesis of Thiomethylnaphthalenes from Propargyl Alcohols DMSO/SOCl2 介导的原炔醇硫代甲基萘合成反应
IF 4.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI: 10.1002/adsc.202401025
Zhihua Wang , Wang‐Fu Liang , Xinglei He , Jingheng Li , Ke‐Yin Ye
{"title":"DMSO/SOCl2‐Mediated Synthesis of Thiomethylnaphthalenes from Propargyl Alcohols","authors":"Zhihua Wang ,&nbsp;Wang‐Fu Liang ,&nbsp;Xinglei He ,&nbsp;Jingheng Li ,&nbsp;Ke‐Yin Ye","doi":"10.1002/adsc.202401025","DOIUrl":"10.1002/adsc.202401025","url":null,"abstract":"<div><div>Herein, we reported the straightforward synthesis of thiomethylnaphthalenes <em>via</em> the reaction of propargyl alcohols with dimethyl sulfoxide/thionyl chloride (DMSO/SOCl<sub>2</sub>), which also provided easy access to deuterated thiomethyl and other thioalkyl scaffolds when deuterated dimethyl sulfoxide and dialkyl sulfoxides were used, respectively. In addition, the thiomethyl group can be readily derivatized to the corresponding sulfoxide, sulfone, and sulfoximine of interesting photophysical properties.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 3","pages":"Article e202401025"},"PeriodicalIF":4.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142385450","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
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