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Copper-Catalyzed Cloke-Wilson Rearrangement for the Synthesis of Dihydrofurans Containing Tetrasubstituted Carbon Atoms 铜催化clok - wilson重排合成含四取代碳原子的二氢呋喃
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-08 DOI: 10.1039/d5qo00401b
Qinqin Cui, Shouang Lan, Xiang Lei, Chao Xu, Chunyun Jiang, Lili Zhao, Liyuan Zhou, Jinggong Liu, Cheng-Zhi Gu, Shuang Yang, Xinqiang Fang
{"title":"Copper-Catalyzed Cloke-Wilson Rearrangement for the Synthesis of Dihydrofurans Containing Tetrasubstituted Carbon Atoms","authors":"Qinqin Cui, Shouang Lan, Xiang Lei, Chao Xu, Chunyun Jiang, Lili Zhao, Liyuan Zhou, Jinggong Liu, Cheng-Zhi Gu, Shuang Yang, Xinqiang Fang","doi":"10.1039/d5qo00401b","DOIUrl":"https://doi.org/10.1039/d5qo00401b","url":null,"abstract":"The Cloke-Wilson rearrangement is a well-established method for synthesizing dihydrofurans, but it primarily results in dihydrofurans lacking tetrasubstituted stereocenters. In this study, we introduce a copper-catalyzed variant of the Cloke-Wilson rearrangement that utilizes 1,1,2,2-tetrasubstituted cyclopropanes. This approach allows for the synthesis of a diverse range of dihydrofurans featuring tetrasubstituted stereocenters, with yields ranging from good to excellent.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"44 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143920228","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Rh(I)-Catalyzed [4+2]-annulation of furan-fused cyclobutanones with alkynes and synthetic applications Rh(I)-催化[4+2]-呋喃-炔烃环丁酮环化及其合成应用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-08 DOI: 10.1039/d5qo00064e
Xinfang Xu, Lixin Qian, Jingjing Huang, Kemiao Hong, Xinyu Jiang, Mengting Liu, Chen Gang, Dorota Gryko
{"title":"Rh(I)-Catalyzed [4+2]-annulation of furan-fused cyclobutanones with alkynes and synthetic applications","authors":"Xinfang Xu, Lixin Qian, Jingjing Huang, Kemiao Hong, Xinyu Jiang, Mengting Liu, Chen Gang, Dorota Gryko","doi":"10.1039/d5qo00064e","DOIUrl":"https://doi.org/10.1039/d5qo00064e","url":null,"abstract":"Fully-substituted aromatic skeletons have received increasing interest from the synthetic chemistry, pharmaceutical and material sciences. However, diversity-oriented construction of these molecules remains challenging due to the lack of effective synthetic building blocks. Herein, we report a Rh(I)-catalyzed [4+2]-annulation reaction of alkynes with furan-fused cyclobutanones (FCBs) for the expeditious assembly of fully-substituted o-quinone methide (o-QM) precursors containing a furan-fused motif under mild conditions. These products could be served a practical and robust synthon for the synthesis of fully-substituted phenols with broad functional group compatibility. Preliminary antitumor activity study indicates that compounds 3d and 5f exhibit high anticancer potency against breast cancer cells (MCF-7 cells, IC50 = 1.87 ± 0.33 μM) and colon cancer cells (HCT-116 cells, IC50 = 1.35 ± 0.15 μM), respectively.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"78 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143920133","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Cs2AgBiBr6-Photocatalytic Trifluoromethylation: Insights in Structural Changes and Applications in Drug Modification cs2agbibr6光催化三氟甲基化：结构变化及其在药物修饰中的应用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-07 DOI: 10.1039/d4qo02237h
Debin Yang, Yalin Guo, Yuanzhe Li, Bo Hu, Bing Yu, Qingchuan Duan
{"title":"Cs2AgBiBr6-Photocatalytic Trifluoromethylation: Insights in Structural Changes and Applications in Drug Modification","authors":"Debin Yang, Yalin Guo, Yuanzhe Li, Bo Hu, Bing Yu, Qingchuan Duan","doi":"10.1039/d4qo02237h","DOIUrl":"https://doi.org/10.1039/d4qo02237h","url":null,"abstract":"The development of new drugs involves complex processes of molecular design, drug screening, and clinical validation, where structural modifications play a crucial role. The trifluoromethyl (CF3) group is significant in medicinal chemistry due to its high lipophilicity, excellent metabolic stability, and enhanced bioavailability. It has a wide range of applications in oncology, cardiovascular diseases and endocrine metabolic diseases. This study introduces a heterogeneous photocatalytic system using double perovskite Cs2AgBiBr6 for various trifluoromethylation reactions. Unlike traditional homogeneous catalysts, this system allows for catalyst recovery and reuse through centrifugation, with the recovered material undergoing structural changes, while decomposition products such as BiBr3 retain their catalytic activity. Operating under mild conditions, it provides a promising strategy for the post-modification of pharmaceutical and natural product molecules, facilitating the synthesis of diverse compounds and expanding organic synthesis methodologies.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143915801","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Catalyst-Controlled 5-exo and 6-endo Cyclization: Regiodivergent Access to Indolinones and Dihydroquinolinones 催化剂控制的5-外显子和6-内环化：吲哚啉酮和二氢喹啉酮的区域发散性
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-07 DOI: 10.1039/d5qo00516g
Xianzhou Zheng, Youzhi Xu, Genping Huang, Weiming Yuan
{"title":"Catalyst-Controlled 5-exo and 6-endo Cyclization: Regiodivergent Access to Indolinones and Dihydroquinolinones","authors":"Xianzhou Zheng, Youzhi Xu, Genping Huang, Weiming Yuan","doi":"10.1039/d5qo00516g","DOIUrl":"https://doi.org/10.1039/d5qo00516g","url":null,"abstract":"Five- and six-membered benzo-fused lactams are important and prevalent scaffolds in many natural products and biologically active compounds. In spite of considerable advances toward their synthesis, the intramolecular alkene functionalization preferably undergoes 5-exo-trig cyclization to afford five-membered ring products, while the kinetically disfavored 6-endo-trig cyclization remains largely elusive. Herein, we reported a novel catalyst-controlled 5-exo/6-endo regiodivergent intramolecular aryl-aminoalkylation of alkenes. The present method affords a variety of five- and six-membered N-heterocycles simultaneously from the same simple starting materials, both products are very useful building blocks in organic synthesis. The computations reveal that the bonding affinity of the alkyl radical to the metal center is the primary factor behind the divergent regioselectivity. The stronger bonding affinity to the Ni center, compared to the Pd center, causes the Ni-catalyzed reaction to initiate with C‒Br bond cleavage to get aryl radical via outer-sphere single electron transfer (OSET) pathway, while the Pd-catalyzed reaction begins with the Giese addition of α-amino radical to the terminal position of alkenes.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"116 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143915798","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Cu-Catalyzed Regiodivergent and Stereoselective Silylation of 2,3-Disubstituted 1,3-Dienes 铜催化2,3-二取代1,3-二烯的区域发散和立体选择性硅基化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-07 DOI: 10.1039/d5qo00512d
Pinglu Zhang, Ziwei Luo, Hao Zeng, Junyang Cen, Ze Li, Guoqiao Lai
{"title":"Cu-Catalyzed Regiodivergent and Stereoselective Silylation of 2,3-Disubstituted 1,3-Dienes","authors":"Pinglu Zhang, Ziwei Luo, Hao Zeng, Junyang Cen, Ze Li, Guoqiao Lai","doi":"10.1039/d5qo00512d","DOIUrl":"https://doi.org/10.1039/d5qo00512d","url":null,"abstract":"Regiodivergent silylation of conjugated dienes represents an elegant and straight forward approach to access diverse organosilicon compounds. While the silylation of 1- or 2- substituted conjugated dienes has been well developed, the silylation of sterically more demanding 2,3-disubstituted dienes was unknown. Here, we disclosed a Cu-catalyzed regiodivergent protosilylation of 2,3-disubstituted dienes, delivering 2,1- and 4,1- protosilylation compounds regioselectively and stereoselectively. Moreover, 4,1-borosilylation with excellent regio- and stereoselectivity was also achieved by the absence of electrophile under similar conditions of 2,1-protosilylation. Our method would like to provide efficient approaches for the synthesis of structurally diverse organosilicon compounds, which would devote in fulfilling the map of conjugated dienes silylation.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"25 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143915799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Palladium-catalyzed site-selective C−H polyfluoroarylation of arenes via aryl thianthrenium salts 钯催化芳基硫鎓盐对芳烃的选择性C - H多氟芳基化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-07 DOI: 10.1039/d5qo00473j
Chen Chen, Jin-Ping Liu, Xin-Yu Hu, Zi-Yi Wang, Xiao-Xu Zhang, Jia-Hui Song, Yan-Ping Zhu, Chunjie Ni, Bolin Zhu
{"title":"Palladium-catalyzed site-selective C−H polyfluoroarylation of arenes via aryl thianthrenium salts","authors":"Chen Chen, Jin-Ping Liu, Xin-Yu Hu, Zi-Yi Wang, Xiao-Xu Zhang, Jia-Hui Song, Yan-Ping Zhu, Chunjie Ni, Bolin Zhu","doi":"10.1039/d5qo00473j","DOIUrl":"https://doi.org/10.1039/d5qo00473j","url":null,"abstract":"This study introduces a novel method for the selective formal C−H/C−H cross-coupling of arenes with polyfluoroarenes via aryl thianthrenium salts under palladium catalysis, resulting in the production of a range of polyfluorinated biaryls in good to excellent yields. The approach demonstrates good environmental sustainability by operating in a one-pot fashion and allowing for the recovery of thianthrene. This two-step process demonstrates its synthetic versatility by enabling the late-stage functionalization of bioactive molecules and the modification of polyfluorinated biaryls.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"14 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143915797","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Access to ester-substituted γ-butyrolactones via photocatalyzed alkoxycarbonylation/lactonization of alkenoic acids 通过光催化烯酸烷氧羰基化/内酯化制备酯取代γ-丁内酯
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-07 DOI: 10.1039/d5qo00520e
Yuping Xiong, Ping Liang, Wenlin Xie, Jian-Qiang Chen, Jie Wu
{"title":"Access to ester-substituted γ-butyrolactones via photocatalyzed alkoxycarbonylation/lactonization of alkenoic acids","authors":"Yuping Xiong, Ping Liang, Wenlin Xie, Jian-Qiang Chen, Jie Wu","doi":"10.1039/d5qo00520e","DOIUrl":"https://doi.org/10.1039/d5qo00520e","url":null,"abstract":"We reported a versatile and concise method to realize the photoredox-induced alkoxycarbonylative lactonization of alkenoic acids for the construction of ester-substituted γ-butyrolactones. This method achieves a multistep cascade reaction by combining photoinduced alkoxycarbonyl radical addition, single-electron oxidization, and lactonization. The reaction shows good compatibility of functional groups with a diverse range of alkoxycarbonyl radical precursors, enabling the efficient introduction of an ester group into the γ-butyrolactone scaffold.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"44 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143915800","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Design and Synthetic Utility of New HAT Organocatalysts Derived from Commercially Available Diamines 由市售二胺衍生的新型HAT有机催化剂的设计与合成应用
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-06 DOI: 10.1039/d5qo00509d
Jingwen Jia, Terumasa Kato, Keiji Maruoka
{"title":"Design and Synthetic Utility of New HAT Organocatalysts Derived from Commercially Available Diamines","authors":"Jingwen Jia, Terumasa Kato, Keiji Maruoka","doi":"10.1039/d5qo00509d","DOIUrl":"https://doi.org/10.1039/d5qo00509d","url":null,"abstract":"A series of hydrogen-atom transfer (HAT) organocatalysts were conveniently prepared from commercially available diamine compounds, and their utility in photoinduced HAT catalysis ability was investigated. The combination of these readily available HAT organocatalysts with the Fukuzumi photoredox catalyst enables efficient and site-selective C−H alkylation of various functionalized substrates ranging from simple hydrocarbons to complex molecules. The site-selective C–H alkylation of multifunctional molecules has also been demonstrated. Notably, the sequential one-pot photoinduced dialkylations of bifunctional substrates can be realized. Mechanistic studies suggested that the 1-naphthylmethyl moiety on one nitrogen atom of the diamine compounds plays a crucial role in the reaction by inducing the facile generation of a cationic aminium radical on the other nitrogen of the diamine as an active intermediate for the HAT process.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"27 20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143910184","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Fluorine-Containing Macrocyclic Peptides and Peptidomimetics 含氟大环肽和拟肽物
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-06 DOI: 10.1039/d5qo00219b
Stefan Roesner, Neshat Rozatian
{"title":"Fluorine-Containing Macrocyclic Peptides and Peptidomimetics","authors":"Stefan Roesner, Neshat Rozatian","doi":"10.1039/d5qo00219b","DOIUrl":"https://doi.org/10.1039/d5qo00219b","url":null,"abstract":"Fluorination plays a vital role in medicinal chemistry due to the unique properties of the fluorine atom. Macrocyclic peptides offer advantageous properties compared to linear peptides in drug discovery. In recent years, the development of fluorinated macrocyclic peptides and peptidomimetics, such as voxilaprevir, MK-0616 and ulimorelin, has highlighted the growing interest in the combination of fluorination and cyclization for tuning the properties of peptidic drug leads. In this review, the effects of fluorination upon biological properties of macrocyclic peptides will be discussed. The use of the fluorine atom as a <small><sup>19</sup></small>F NMR spectroscopy probe for conformational studies of macrocyclic peptides will be reviewed. Finally, macrocyclic peptides containing the radionucleotide <small><sup>18</sup></small>F as PET imaging agents will be highlighted.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"110 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143910185","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Synergistic catalytic allenylic alkylation for stereodivergent construction of allenes bearing 1,3-axial central chirality 具有1,3轴中心手性的烯丙烯立体发散结构的协同催化烷基化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-05-05 DOI: 10.1039/d5qo00467e
Min Chen, Yuzhen Li, Jun He, Lili Lin, Liang-Wen Feng, Xiaohua Liu
{"title":"Synergistic catalytic allenylic alkylation for stereodivergent construction of allenes bearing 1,3-axial central chirality","authors":"Min Chen, Yuzhen Li, Jun He, Lili Lin, Liang-Wen Feng, Xiaohua Liu","doi":"10.1039/d5qo00467e","DOIUrl":"https://doi.org/10.1039/d5qo00467e","url":null,"abstract":"A highly efficient asymmetric allenylic alkylation for the construction of allenes bearing allenyl axial and central chirality through synergistic Ni/Pd catalysis has been developed. This catalytic protocol operates smoothly under one-pot, additive-free conditions, offering exceptional step efficiency and high atomic economy. A wide range of chiral two or three-substituted allenes bearing multi-substituted acyclic or cyclic carbonyl moieties were obtained with excellent reactivity and stereoselectivity under this dual catalytic system. The stereodivergent synthesis was successfully realized, delivering all stereoisomers in high yields. Diastereoselectivity reversal manifested that the chiral Lewis acid catalyst could effectively override the stereocontrol capability of the chiral plladium catalyst itself, enabling access to dynamically disfavored diastereomers with high enantiocontrol. Gram-scale synthesis and further transformation experiment demonstrate the potential utility of this method.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"137 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143910418","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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