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Dual photoredox/copper-catalyzed selective difluoromethylthiolation of remote unactivated C(sp3)-H bonds at room temperature. 室温下远端非活化C(sp3)-H键的双光氧化还原/铜催化选择性二氟甲基硫基化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00257e
Shengwen Li, Guanfeng Ji, Wengui Wang, Shoufeng Wang
{"title":"Dual photoredox/copper-catalyzed selective difluoromethylthiolation of remote unactivated C(sp<sup>3</sup>)-H bonds at room temperature.","authors":"Shengwen Li, Guanfeng Ji, Wengui Wang, Shoufeng Wang","doi":"10.1039/d5ob00257e","DOIUrl":"https://doi.org/10.1039/d5ob00257e","url":null,"abstract":"<p><p>A photocatalysis/copper dual-catalyzed difluoromethylthiolation of remote unactivated C(sp<sup>3</sup>)-H bonds using <i>N</i>-fluorosulfonamides was reported. The combination of photoredox and copper catalysis led to mild reaction conditions with a broad substrate scope. Luminescence quenching experiments revealed that both <i>N</i>-fluorosulfonamides and the copper catalyst could quench the excited state of the Ru complex. Primary, secondary and tertiary C(sp<sup>3</sup>)-H bonds could be transformed, offering an efficient way to construct difluoromethylthio-bearing compounds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148720","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
Ribosomal incorporation of N-acetyl-3,5-bis(chloromethyl)benzylthio-L-alanine for developing an mRNA-displayed bicyclic peptide library cyclized via 1,3,5-tris(methyl)benzene. 核糖体结合n -乙酰-3,5-二（氯甲基）苄基硫代- l-丙氨酸，形成经1,3,5-三（甲基）苯环化的mrna双环肽文库。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00693g
Maolin Li, Haipeng Yu, Jie Cheng, Wenfeng Cai, Youming Zhang, Yizhen Yin
{"title":"Ribosomal incorporation of <i>N</i>-acetyl-3,5-bis(chloromethyl)benzylthio-L-alanine for developing an mRNA-displayed bicyclic peptide library cyclized <i>via</i> 1,3,5-tris(methyl)benzene.","authors":"Maolin Li, Haipeng Yu, Jie Cheng, Wenfeng Cai, Youming Zhang, Yizhen Yin","doi":"10.1039/d5ob00693g","DOIUrl":"https://doi.org/10.1039/d5ob00693g","url":null,"abstract":"<p><p>We report a novel method for constructing an mRNA-displayed bicyclic peptide library cyclized through 1,3,5-tris(methyl)benzene by ribosomally incorporating <i>N</i>-acetyl-3,5-bis(chloromethyl)benzylthio-L-alanine, enabling the selection of bicyclic peptides against specific targets. Using this method, we successfully identified bicyclic peptides that bind to human Trop2 and VEGF165, providing a new strategy for selecting bicyclic peptides cyclized by trimethylbenzene.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148815","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
Nickel-catalyzed reductive coupling of 2-pyridyl esters with unactivated alkyl chlorides: a universal synthesis of aryl-alkyl and dialkyl ketones via dynamic halide exchange. 镍催化的2-吡啶酯与未活化的烷基氯的还原偶联：通过动态卤化物交换合成芳烷基酮和二烷基酮的通用方法。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00670h
Cong Guo, Zhen-Ying Wang, Wen-Heng Liu, Shi-Zheng Liu, Yi-Zheng Cheng, Qiang Li, Jianmin Dou
{"title":"Nickel-catalyzed reductive coupling of 2-pyridyl esters with unactivated alkyl chlorides: a universal synthesis of aryl-alkyl and dialkyl ketones <i>via</i> dynamic halide exchange.","authors":"Cong Guo, Zhen-Ying Wang, Wen-Heng Liu, Shi-Zheng Liu, Yi-Zheng Cheng, Qiang Li, Jianmin Dou","doi":"10.1039/d5ob00670h","DOIUrl":"https://doi.org/10.1039/d5ob00670h","url":null,"abstract":"<p><p>Direct synthesis of ketones <i>via</i> a nickel-catalyzed reductive coupling between aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters and unactivated 1°, 2°-alkyl chlorides has been reported. This approach provides a highly efficient catalytic system to synthesize aryl-alkyl and dialkyl ketones in moderate to excellent yields with good functional group tolerance from easily accessible starting materials. Mechanistic studies reveal that a TBAI-mediated dynamic halide exchange process maintains a controlled low concentration of alkyl iodides, balancing the reactivity and cross-selectivity of alkyl chlorides.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148808","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
Systematic studies toward the synthesis of D-galactosamine-containing coumarin glycosides. 含d -半乳糖胺香豆素糖苷合成的系统研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00746a
Hannah S Wootton, Gavin J Miller
{"title":"Systematic studies toward the synthesis of D-galactosamine-containing coumarin glycosides.","authors":"Hannah S Wootton, Gavin J Miller","doi":"10.1039/d5ob00746a","DOIUrl":"https://doi.org/10.1039/d5ob00746a","url":null,"abstract":"<p><p>An <i>O</i>-glycosylation method for accessing coumarin glycosides is presented. We report the reaction of 6,8-difluoro-7-hydroxy-4-methylcoumarin and 4-methylumbelliferone with a variety of glycosyl imidate donors using BF<sub>3</sub>·Et<sub>2</sub>O as activator to access a series of coumarin glycosides in 64%-76% isolated yields. Several reaction parameters are evaluated including promotors, temperature and reagent equivalents. Following initial methodology development using simple D-glucose donors, D-galactosamino mono- and disaccharides are explored as substrates, showcasing applicability towards late-stage transformation of biologically relevant chondroitin sulfate glycosides. Glycosylation diastereoselectivity trends were also considered, proposing that the identity of the D-galactosamino <i>N</i>-protecting group and the coumarin acceptor contribute to observed anomeric product ratios. This methodology provides a convenient access to D-galactosamino-coumarin glycoconjugates and provides a benchmark for the development of related systems for biological evaluation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148817","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
Mild trifluoromethylsulfinylation of alcohols and amines via N-hydroxyphthalimide-O-trifluoromethanesulfinate. 通过n -羟基邻苯二胺- o -三氟甲烷磺酸盐对醇和胺进行轻度三氟甲基亚砜化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00566c
Liuqing Yang, Hongwei Wang, Xinyu Wang, Menglin Jiang, Dianhu Zhu
{"title":"Mild trifluoromethylsulfinylation of alcohols and amines <i>via N</i>-hydroxyphthalimide-<i>O</i>-trifluoromethanesulfinate.","authors":"Liuqing Yang, Hongwei Wang, Xinyu Wang, Menglin Jiang, Dianhu Zhu","doi":"10.1039/d5ob00566c","DOIUrl":"https://doi.org/10.1039/d5ob00566c","url":null,"abstract":"<p><p>Direct and efficient trifluoromethylsulfinylation of alcohols and amines is highly desirable in the drug design field. Herein, we report a simple trifluoromethylsulfinylation of alcohols and amines at room temperature under remarkably mild conditions, enabled by a powerful <i>N</i>-hydroxyphthalimide-<i>O</i>-trifluoromethanesulfinate. This protocol was conducted under activator and additive-free conditions, and is effective for the direct transfer of the CF<sub>3</sub>S(O) group to a series of alkyl alcohols, alkyl amines and aromatic amines with good to excellent yields and superb functional group tolerance, as well as facile extension to late-stage trifluoromethylsulfinylation of complex biologically active alcohols and amines. Preliminary mechanistic experiments suggest that the direct nucleophilic attack of the highly active <i>N</i>-hydroxyphthalimide-<i>O</i>-trifluoromethanesulfinate is the key factor for the success of the electrophilic trifluoromethylsulfinylation of alcohols and amines in the absence of any activators or additives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148804","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
n Bu4NBr-catalyzed esterification of methoxyarenes with acyl bromide. n bu4nbr催化甲氧基芳烃与酰基溴的酯化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-27 DOI: 10.1039/d5ob00612k
Ting Sun, Wen Chao Zhu, Qin Zhu, Shao Yin Wang, Guo Dong Wang, Jiang-Fei Li
{"title":"<sup><i>n</i></sup> Bu<sub>4</sub>NBr-catalyzed esterification of methoxyarenes with acyl bromide.","authors":"Ting Sun, Wen Chao Zhu, Qin Zhu, Shao Yin Wang, Guo Dong Wang, Jiang-Fei Li","doi":"10.1039/d5ob00612k","DOIUrl":"https://doi.org/10.1039/d5ob00612k","url":null,"abstract":"<p><p>The catalytic esterification of methoxyarenes remains challenging, especially for C(sp<sup>3</sup>)-O bond functionalization. Herein, we report a simple and efficient method using <sup><i>n</i></sup>Bu<sub>4</sub>NBr as a catalyst to directly convert methoxyarenes and acyl bromides into esters under solvent-free conditions. This strategy provides a simple and efficient approach, achieving yields of up to 95%.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148717","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
Recent applications of Cyrene as a chiral synthon. 昔兰尼手性合成物的最新应用。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00642b
Yu A Khalilova, L Kh Faizullina
{"title":"Recent applications of Cyrene as a chiral synthon.","authors":"Yu A Khalilova, L Kh Faizullina","doi":"10.1039/d5ob00642b","DOIUrl":"https://doi.org/10.1039/d5ob00642b","url":null,"abstract":"<p><p>Dihydrolevoglucosenone (Cyrene™) is a unique chiral molecule with great synthetic potential. Currently, Cyrene has been successfully used as a dipolar aprotonic solvent with green chemistry requirements, which is very important for both medicine and industry. There are several review articles on this topic, which we have referenced in this article. In this review, we describe the prospect of using Cyrene as a chiral molecule in organic synthesis, including an emphasis on the route to practically important objects based on it. The review presents chemical transformations of Cyrene by reactive centers (carbonyl and methylene groups, acetal center, anhydro bridge) with an eye to valuable chiral molecules and discusses the mechanism of some interesting transformations. We hope that the review will be useful to scientists working not only in organic but also in medicinal and polymer chemistry. The review summarizes the literature data for the last 10 years, with the rare exception of earlier works in view of the importance of using the published material.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126110","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
Catalytic dynamic kinetic reductive addition of simple aldehydes and aldimines with heterobiaryl triflates: harnessing both central and axial chirality. 简单醛和醛胺与三氟酸杂二芳酯的催化动力学还原加成：利用中心手性和轴向手性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00521c
Hui Ni, Anyao Liu, Xiaoying Fu, Xinyi Zhang, Xiaowen Xue, Xiang Lyu, Aijun Lin, Yuli He
{"title":"Catalytic dynamic kinetic reductive addition of simple aldehydes and aldimines with heterobiaryl triflates: harnessing both central and axial chirality.","authors":"Hui Ni, Anyao Liu, Xiaoying Fu, Xinyi Zhang, Xiaowen Xue, Xiang Lyu, Aijun Lin, Yuli He","doi":"10.1039/d5ob00521c","DOIUrl":"https://doi.org/10.1039/d5ob00521c","url":null,"abstract":"<p><p>A nickel-catalyzed intramolecular dynamic kinetic resolution (DKR) strategy has been developed for the enantioselective synthesis of axially chiral heterobiaryls from racemic azabiaryl triflates. Using a reductive addition mechanism, this method controls both axial and central chirality, offering broad substrate scope, excellent enantioselectivity, and atroposelectivity. The resulting chiral heterobiaryls were effectively employed as organocatalysts and chiral ligands in asymmetric transformations, highlighting their synthetic utility. Mechanistic studies indicate a synergy between kinetic resolution and nickel-mediated stereochemical inversion, addressing challenges in concurrent axial and stereochemical control.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126381","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
Rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes to access fused naphthalenes. 铑催化3-芳基异恶唑与1,6-二炔序贯双碳氢环化反应得到熔融萘。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00466g
Ramesh Kotipalli, T Mahipal Reddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
{"title":"Rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes to access fused naphthalenes.","authors":"Ramesh Kotipalli, T Mahipal Reddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy","doi":"10.1039/d5ob00466g","DOIUrl":"https://doi.org/10.1039/d5ob00466g","url":null,"abstract":"<p><p>Selective dual C-H annulations with 1,<i>n</i>-diunsaturated systems represent a powerful tool for constructing multicyclic scaffolds in an expeditious manner. Here, we report a rhodium catalyzed sequential dual C-H annulation of 3-arylisoxazoles with 1,6-diynes for napthofused polycyclic systems. Some kinetic isotopic experiments were carried out to understand the reaction mechanism and some downstream experiments were conducted to demonstrate the potential of the methodology. The method features a broad substrate scope and scale-up capability.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126113","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
Superacid-catalysed α-deuteration of ketones with D2O. 超强酸催化D2O对酮的α-氘化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-23 DOI: 10.1039/d5ob00683j
Haiying Yuan, Kaibo Xu, Jinling Li, Teck-Peng Loh, Zhenguo Zhang, Zhenhua Jia
{"title":"Superacid-catalysed α-deuteration of ketones with D<sub>2</sub>O.","authors":"Haiying Yuan, Kaibo Xu, Jinling Li, Teck-Peng Loh, Zhenguo Zhang, Zhenhua Jia","doi":"10.1039/d5ob00683j","DOIUrl":"https://doi.org/10.1039/d5ob00683j","url":null,"abstract":"<p><p>In this study, we present a superacid catalyzed protocol for the α-deuteration of ketones with D<sub>2</sub>O using [Ph<sub>3</sub>C]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup> as a pre-catalyst to generate <i>in situ</i> the superacidic species [D]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup>. The features of this catalytic process include simple manipulation, high deuteration efficiency (up to 99%), excellent functional group compatibility and a broad substrate scope, including 30 substrates comprising common building blocks and bioactive molecules like pentoxifylline. Moreover, the avoidance of toxic reagents enables sustainable access to deuterated products, demonstrating the method's practical potential for use in mechanistic studies and pharmaceutical applications.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144126115","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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