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Generation of C(sp3)–CAr bonds in the synthesis of triarylmethanes (TRAMs): comprehensive progress since 2009
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-27 DOI: 10.1039/D4OB02069C
Yaqoob A. Teli, Kamal Kant, S. Aleena Chanu, Nayyef Aljaar and Chandi C. Malakar
{"title":"Generation of C(sp3)–CAr bonds in the synthesis of triarylmethanes (TRAMs): comprehensive progress since 2009","authors":"Yaqoob A. Teli, Kamal Kant, S. Aleena Chanu, Nayyef Aljaar and Chandi C. Malakar","doi":"10.1039/D4OB02069C","DOIUrl":"10.1039/D4OB02069C","url":null,"abstract":"<p >Triarylmethanes are useful compounds in materials science and medicinal chemistry. These moieties are important constituents of dyes and pharmaceuticals. These scaffolds are synthesized either by Friedel–Crafts alkylation of aldehydes and arenes or by the functionalization of diarylmethanes. The development of effective catalytic systems and the discovery of highly regio- and stereoselective methods using Brønsted or Lewis acid catalysts represent particularly important achievements in this field. This review explores the detailed documentation of the various catalytic strategies witnessed since 2009 for the synthesis of triarylmethanes, which could arouse the interest of readers in organic synthesis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 15","pages":" 3492-3519"},"PeriodicalIF":2.9,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622832","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Photoredox nickel-catalyzed radical cyclization of N-arylacrylamides with alkyl bromides†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d5ob00078e
Yan-Ling Liu , Liu-Shuo Shi , Xian-Chen He , Jie Gao , Ke-Rong Li , Hao-Yue Xiang , Kai Chen , Hua Yang
{"title":"Photoredox nickel-catalyzed radical cyclization of N-arylacrylamides with alkyl bromides†","authors":"Yan-Ling Liu ,&nbsp;Liu-Shuo Shi ,&nbsp;Xian-Chen He ,&nbsp;Jie Gao ,&nbsp;Ke-Rong Li ,&nbsp;Hao-Yue Xiang ,&nbsp;Kai Chen ,&nbsp;Hua Yang","doi":"10.1039/d5ob00078e","DOIUrl":"10.1039/d5ob00078e","url":null,"abstract":"<div><div>3,3-Disubstituted oxindoles constitute a significant class of biologically active molecules, often found in a wide range of bioactive compounds. In this work, we present a photoredox nickel-catalyzed intermolecular cyclization between <em>N</em>-arylacrylamides and readily accessible alkyl bromides, which affords a diverse range of 3,3-disubstituted oxindoles in moderate to high yields. Our mechanistic studies reveal that the reduction of alkyl bromides <em>via</em> single-electron transfer from a reactive Ni(<span>i</span>) species is a critical step in driving this radical cascade transformation. This approach offers several advantages, including mild reaction conditions, broad functional group tolerance, and a simple workup procedure.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3126-3130"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143497689","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Selective C(sp2)–H bond radical thiocyanation of cyclic α,β-unsaturated ketones†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d5ob00065c
Mengyi Li , Yu Zhang , Yu Zhao , Jingfu Zhu , Yu Cheng , Wei Li , Di Wu
{"title":"Selective C(sp2)–H bond radical thiocyanation of cyclic α,β-unsaturated ketones†","authors":"Mengyi Li ,&nbsp;Yu Zhang ,&nbsp;Yu Zhao ,&nbsp;Jingfu Zhu ,&nbsp;Yu Cheng ,&nbsp;Wei Li ,&nbsp;Di Wu","doi":"10.1039/d5ob00065c","DOIUrl":"10.1039/d5ob00065c","url":null,"abstract":"<div><div>This study presents an AIBN catalyzed radical thiocyanation reaction, which efficiently enables the thiocyanation of C(sp<sup>2</sup>)–H bonds in cyclic conjugated unsaturated alkenes, such as uracil and quinolinone derivatives. The method demonstrates excellent substrate versatility, successfully synthesizing 5-thiocyanato derivatives of uracil and quinolinone compounds. It also shows remarkable tolerance to a wide range of functional groups, with yields ranging from 41% to 99%. Moreover, the reaction can be extended to other halogenation-based functionalization reactions, highlighting its practical applicability.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3107-3111"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143539574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Stereoselective synthesis of a KRASG12C inhibitor with a quinoline-piperazine scaffold†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d4ob02104e
Ying Hu , Jing Zheng , Yin-Jun Chen , Wei-Yi Pu , Yan-Jun Xu , Lin Dong
{"title":"Stereoselective synthesis of a KRASG12C inhibitor with a quinoline-piperazine scaffold†","authors":"Ying Hu ,&nbsp;Jing Zheng ,&nbsp;Yin-Jun Chen ,&nbsp;Wei-Yi Pu ,&nbsp;Yan-Jun Xu ,&nbsp;Lin Dong","doi":"10.1039/d4ob02104e","DOIUrl":"10.1039/d4ob02104e","url":null,"abstract":"<div><div>We developed a novel synthetic route for the KRAS<sub>G12C</sub> inhibitor, focusing on the efficient construction of its central quinoline scaffold. The method offers several advantages: eliminates the formation of regioselective by-products and avoids the use of high temperatures and nitric acid. The last step of the overall route enables gentle hydrolysis of phenyl esters with methanol and potassium carbonate, which greatly reduces the occurrence of side reactions. In addition, the stereoisomers were successfully separated by silica gel column chromatography.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3194-3198"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143571726","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
A MnCl2-catalyzed synthesis of aldehydes from organohalides by using samarium metal in DMF†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d5ob00193e
Hongping Chen , Mingzhong Mi , Chao Wang , Aowen Li , Yan Qi , Yongjun Liu
{"title":"A MnCl2-catalyzed synthesis of aldehydes from organohalides by using samarium metal in DMF†","authors":"Hongping Chen ,&nbsp;Mingzhong Mi ,&nbsp;Chao Wang ,&nbsp;Aowen Li ,&nbsp;Yan Qi ,&nbsp;Yongjun Liu","doi":"10.1039/d5ob00193e","DOIUrl":"10.1039/d5ob00193e","url":null,"abstract":"<div><div>A novel coupling reaction between organohalides and <em>N</em>,<em>N</em>-dimethylformamide (DMF) catalyzed by MnCl<sub>2</sub> was investigated in the presence of samarium metal under mild conditions. A variety of aliphatic, aromatic and heterocyclic aldehydes were produced with good yields in one pot. Bromo substrates showed the most efficient reactivity among the organohalides used in the experiments, and 10 mol% MnCl<sub>2</sub> was sufficient to catalyze the reaction. The reaction proceeds smoothly and can be scaled up to the gram level. This is the first combination of samarium and manganese in organic synthesis. Unlike cuprous iodide or silver nitrate, manganese chloride can promote the formation of aliphatic aldehydes. The reaction mechanism is also discussed.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3137-3142"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143539560","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Energy transfer-mediated carbonylimination of alkenes using a bifunctional reagent† 使用双功能试剂以能量转移为介导的烯烃羰基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d5ob00123d
Zetian Sun , Weishu Yu , Xiaoqing Li , Xiangsheng Xu , Xiaohua Du
{"title":"Energy transfer-mediated carbonylimination of alkenes using a bifunctional reagent†","authors":"Zetian Sun ,&nbsp;Weishu Yu ,&nbsp;Xiaoqing Li ,&nbsp;Xiangsheng Xu ,&nbsp;Xiaohua Du","doi":"10.1039/d5ob00123d","DOIUrl":"10.1039/d5ob00123d","url":null,"abstract":"<div><div>A photoinduced EnT-mediated generation of acyl radicals has been accomplished using rationally designed acyl oxime ether reagents under metal-free conditions. This approach offers a mild and practical method for the synthesis of valuable β-aminoketones.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3093-3096"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143522209","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Total synthesis of (±)-halichonine B†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d5ob00145e
Fumihiko Yoshimura , Masaya Uchida , Kaori Aratame , Hitoshi Ouchi , Makoto Inai , Mitsuru Kondo , Ryo Takita , Toshiyuki Kan
{"title":"Total synthesis of (±)-halichonine B†","authors":"Fumihiko Yoshimura ,&nbsp;Masaya Uchida ,&nbsp;Kaori Aratame ,&nbsp;Hitoshi Ouchi ,&nbsp;Makoto Inai ,&nbsp;Mitsuru Kondo ,&nbsp;Ryo Takita ,&nbsp;Toshiyuki Kan","doi":"10.1039/d5ob00145e","DOIUrl":"10.1039/d5ob00145e","url":null,"abstract":"<div><div>The stereocontrolled total synthesis of (±)-halichonine B was achieved in 18 steps for the longest linear sequence. This synthesis features the stereoselective construction of a <em>trans</em>-fused dehydrodecalin framework containing three consecutive stereocenters through sequential intramolecular conjugate additions. Additionally, the strategic use of nitrobenzenesulfonamides enabled the efficient installation of a branched diamine moiety.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3076-3080"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555319","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 β-rhamnose containing ready to conjugate tetrasaccharide repeating unit corresponding to the K141 CPS of Acinetobacter baumannii KZ1106†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d5ob00161g
Swapnendu Pramanik , Abhishek Santra
{"title":"Synthesis of β-rhamnose containing ready to conjugate tetrasaccharide repeating unit corresponding to the K141 CPS of Acinetobacter baumannii KZ1106†","authors":"Swapnendu Pramanik ,&nbsp;Abhishek Santra","doi":"10.1039/d5ob00161g","DOIUrl":"10.1039/d5ob00161g","url":null,"abstract":"<div><div>Herein, we developed an efficient chemical synthetic strategy of a tetrasaccharide repeating unit corresponding to the K141 type capsular polysaccharide of <em>Acinetobacter baumannii</em> KZ1106. The synthesis of the propylamine-linked tetrasaccharide is executed through an efficient [2 + 2] block glycosylation strategy. The construction of a synthetically challenging β-<span>l</span>-rhamnopyranosyl linkage was achieved through ‘armed-disarmed’ glycosylation, with the assistance of a picolinoyl group located remotely through the hydrogen bond mediation effect. The conjugation-ready target oligosaccharide presents a compelling opportunity for the subsequent formation of glycoconjugates with an appropriate aglycon.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3199-3207"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143584040","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation† 通过炔[2 + 2 + 2]环三聚化合成二氢甘比坦。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d5ob00162e
Pattarakiat Seankongsuk , Patcharaporn Sae-Lao , Shi He , Veronica Pereira , Roderick W. Bates
{"title":"Synthesis of dihydrogambirtannine by alkyne [2 + 2 + 2]-cyclotrimerisation†","authors":"Pattarakiat Seankongsuk ,&nbsp;Patcharaporn Sae-Lao ,&nbsp;Shi He ,&nbsp;Veronica Pereira ,&nbsp;Roderick W. Bates","doi":"10.1039/d5ob00162e","DOIUrl":"10.1039/d5ob00162e","url":null,"abstract":"<div><div>The first asymmetric synthesis of (−)-dihydrogambirtannine has been achieved using nucleophilic addition to a chiral sulfinyl imine to establish the stereogenic centre and [2 + 2 + 2] alkyne cyclotrimerisation to construct the aromatic E ring.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3131-3136"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/ob/d5ob00162e?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143497694","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 the synthesis of chalcogenylated heterocycles obtained by chalcogenocyclization
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-02-26 DOI: 10.1039/d4ob01691b
Ricardo H. Bartz , Paola S. Hellwig , Kethelyn M. Rosa , Márcio S. Silva , Eder J. Lenardão , Raquel G. Jacob , Gelson Perin
{"title":"Recent advances in the synthesis of chalcogenylated heterocycles obtained by chalcogenocyclization","authors":"Ricardo H. Bartz ,&nbsp;Paola S. Hellwig ,&nbsp;Kethelyn M. Rosa ,&nbsp;Márcio S. Silva ,&nbsp;Eder J. Lenardão ,&nbsp;Raquel G. Jacob ,&nbsp;Gelson Perin","doi":"10.1039/d4ob01691b","DOIUrl":"10.1039/d4ob01691b","url":null,"abstract":"<div><div>Heterocyclic molecules containing organochalcogens are important scaffolds that have attracted scientific interest due to their remarkable pharmacological properties. As a consequence, in recent years several protocols have been developed for the synthesis of this class of compounds. More specifically, cyclization reactions have become a powerful tool in the synthesis of heterocycles containing two or more chalcogen atoms. This review summarizes the recent advances in the synthesis of heterocycles containing two or more chalcogens (S, Se, and Te), through a wide diversity of cyclization reactions with different substrates, with emphasis on cyclization reactions of chalcogenoalkynes and alkenes in chalcogenocyclization reactions, highlighting their scope, main advantages, synthetic differences, and limitations.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 2997-3028"},"PeriodicalIF":2.9,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389562","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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