Organic chemistry frontiers : an international journal of organic chemistry最新文献_第9页

Metal and photocatalyst-free alkylboration of [1.1.1]propellane enabled by red-light-induced electron transfer† 通过红光诱导的电子转移实现 [1.1.1]propellane 的无金属和无光催化剂烷基硼化

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00357a

Yuying Wang , Jianyang Dong , Yulin Xiao , Zhilin Wang , Weilin Wu , Dong Xue

{"title":"Metal and photocatalyst-free alkylboration of [1.1.1]propellane enabled by red-light-induced electron transfer†","authors":"Yuying Wang , Jianyang Dong , Yulin Xiao , Zhilin Wang , Weilin Wu , Dong Xue","doi":"10.1039/d5qo00357a","DOIUrl":"10.1039/d5qo00357a","url":null,"abstract":"<div><div>Highly strained 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs) have emerged as bioisosteres of <em>para</em>-disubstituted benzene rings because of the ability of the former to impart valuable pharmacokinetic properties. However, challenges such as the lack of convenient and green access to useful BCP building blocks continue to hinder early-stage discovery research. Herein, we report a metal and photocatalyst-free method for deaminative borylation of [1.1.1]propellane for the synthesis of BCP boronates. This method involves the generation of alkyl or α-ester alkyl radicals <em>via</em> red-light-induced formation of a ternary electron donor–acceptor complex between a Katritzky salt, Cs<sub>2</sub>CO<sub>3</sub>, and B<sub>2</sub>pin<sub>2</sub>. Selective addition of the radicals to [1.1.1]propellane produces BCP radicals that undergo polarity-matched addition to B<sub>2</sub>pin<sub>2</sub>, leading to BCP difunctionalization. The method, which does not require metals or photocatalysts, allows for direct construction of alkyl species from readily available amines and α-amino acids and concurrent introduction of synthetically versatile pinacol boronate (Bpin) groups onto the BCP substructure. We demonstrate the synthetic utility of our method through several important transformations of the Bpin and hydroxyl functional groups of the products, including photoinduced cross-coupling reactions of BCP-BF<sub>3</sub>K derived from BCP-Bpin.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4050-4057"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143775779","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Palladium-catalysed asymmetric regioselective hydroamination of dienoates† 钯催化的脂酸酯不对称区域选择性氢胺化反应

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00402k

Bao-Xin Liu , Xin-Ting Qin , Shi-Cun Li , Lei Zhu , Qin Ouyang , Wei Du , Ying-Chun Chen

引用次数: 0

Thrysaxinones A–F: antibacterial phloroglucinol-terpenoid adducts from Thryptomene saxicola† 赤霉素A - F：从赤霉中提取的抗菌间苯三酚萜类加合物

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00172b

Wei-Fang Su , Ni-Ping Li , Rui-Qin Cui , Fen Liu , Mu Chen , Xin-Yue Wu , Min-Jing Cheng , Jia-Qing Cao , Wei Huang , Xiao-Qi Zhang , Wen-Cai Ye , Lei Wang

{"title":"Thrysaxinones A–F: antibacterial phloroglucinol-terpenoid adducts from Thryptomene saxicola†","authors":"Wei-Fang Su , Ni-Ping Li , Rui-Qin Cui , Fen Liu , Mu Chen , Xin-Yue Wu , Min-Jing Cheng , Jia-Qing Cao , Wei Huang , Xiao-Qi Zhang , Wen-Cai Ye , Lei Wang","doi":"10.1039/d5qo00172b","DOIUrl":"10.1039/d5qo00172b","url":null,"abstract":"<div><div>Thrysaxinones A–F (), six new phloroglucinol-terpenoid adducts (PTAs), were isolated from <em>Thryptomene saxicola</em>. Their structures and absolute configurations were elucidated by extensive spectroscopic analysis, X-ray crystallography, and quantum chemical calculations. Compounds represent unprecedented PTAs with gorgonane- or oplopane-type sesquiterpenoid moieties. Notably, compound features an unusual 11-oxa-tricyclo[6.2.1.0<sup>4,9</sup>]undecane core. Compound is a unique PTA with a new carbon skeleton formed by an acylphloroglucinol unit coupled with a bicyclogermacrene-type sesquiterpenoid moiety. The plausible biogenetic pathways for compounds were proposed. Moreover, compounds , , , and exhibited significant antibacterial activities against clinical methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) strains. Compound , the most potent one, could rapidly and effectively eradicate bacteria by inducing hyperpolarization and disrupting cell membrane integrity.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4037-4044"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767063","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Ni-catalyzed regio- and diastereoselective syn-alkynylamination of unactivated alkenes using alkylamine sources† 镍催化非活化烯烃与烷基胺源的区域和非对映选择性同构烷基胺层合反应

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00194c

Yixuan Wan , Cong Lin , Yihuan Cheng , Liang Shen

引用次数: 0

Construction of chiral γ-lactam scaffolds via asymmetric cascade [3 + 2] annulation of N-alkoxyacrylamides catalyzed by a chiral-at-metal rhodium complex† 手性金属铑配合物催化n -烷氧基丙烯酰胺不对称级联[3+2]环构建手性γ-内酰胺支架

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00276a

Wan-Shun Cheng , Yong-Bing Ke , Yang Chen , Hui-Ting Cui , Rui-Qiu Zhang , He-Lin Lu , Ping Xue , Xiao-Bo Wang , Shi-Wu Li , Jun Gong

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Dimethoxytetramethyldisilane: overcoming the limitations of palladium-catalyzed C–H silacyclization of 2-iodobiphenyls† 二甲氧基四甲基二硅烷：克服钯催化的2-碘联苯C-H硅环化的局限性

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00249d

Zhengrui Zhou , Xuliang Tan , Shuyun Peng , Yun Liang , Yuan Yang

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Iron-catalyzed regioselective carboazidation of alkenes for the synthesis of multi-substituted cyclobutylamines† 铁催化烯烃区域选择性碳氮化反应合成多取代环丁胺

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00173k

Yufei Li , Yajun Li , Hongli Bao

引用次数: 0

Recent developments in organic synthesis for constructing carbon frameworks using transposition strategies 利用转位策略在有机合成中构建碳框架的最新进展

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00163c

Savita Narayanrao Gat , Piyusa Priyadarsan Pattanaik , Rambabu Dandela

{"title":"Recent developments in organic synthesis for constructing carbon frameworks using transposition strategies","authors":"Savita Narayanrao Gat , Piyusa Priyadarsan Pattanaik , Rambabu Dandela","doi":"10.1039/d5qo00163c","DOIUrl":"10.1039/d5qo00163c","url":null,"abstract":"<div><div>Transposition reaction has remained as the versatile and eco-friendly approach in organic synthesis, providing a sustainable route for generating complex molecules with lower negative impact on the environment. In particular, transposition reaction facilitates selective rearrangement of molecular fragments, which aid the strategic bond disconnections that cover the synthetic pathways and improve the atom economy of the reaction. Moreover, it minimizes the need for high-energy intermediates or reagents, where as in transposition methods support green chemistry principles, including waste reduction, energy efficiency, and sustainability. Besides, transposition strategies render the reaction to occur under mild conditions, making them appealing alternatives to conventional synthetic methods. Due to the limited availability of well-structured reviews in this domain, we first present distinct classes of transposition reactions, with an emphasis on the influence of catalytic systems, reaction conditions, and substrate characteristics on both efficiency and selectivity predominantly relevant to the individual significance of carbonyl, alkene, chirality, allylic alcohol, and functional group transpositions. The versatility of these reactions for creating diverse molecular scaffolds from readily available substrates opens up new avenues for the synthesis of bioactive compounds, pharmaceuticals, natural products and merely represent a compelling tool for advancing greener, more efficient approaches for organic synthesis.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4151-4180"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143661088","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 Z-alkenylative cross-coupling via β-alkenyl elimination of Z-allylic alcohols† 钯通过β-烯基消除z -烯丙醇催化z -烯基化交叉偶联

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00110b

Xue-Mei Huang , Cheng Liang , Si-Qi Xiong , Xue Zhang , Kai-Xian Ma , Qing-Hua Li , Tang-Lin Liu

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Metallaphotoredox-enabled enantioselective aryldifluoromethyl-alkynylation of alkenes via C(sp3)–F bond activation† 通过C(sp3)-F键激活的金属光氧化还原使芳基二氟甲基烷基化烯烃的对映选择性

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00370a

Jialin Huang , Liying Fu , Xiaofei Zhao , Xingda Zhao , Zhanyong Tang , Xiaoqiang Ma , Depeng Zhao

{"title":"Metallaphotoredox-enabled enantioselective aryldifluoromethyl-alkynylation of alkenes via C(sp3)–F bond activation†","authors":"Jialin Huang , Liying Fu , Xiaofei Zhao , Xingda Zhao , Zhanyong Tang , Xiaoqiang Ma , Depeng Zhao","doi":"10.1039/d5qo00370a","DOIUrl":"10.1039/d5qo00370a","url":null,"abstract":"<div><div>Due to the prevalence of trifluoromethylarene (ArCF<sub>3</sub>) units in drug-related molecules, direct late-stage functionalization of C(sp<sup>3</sup>)–F bonds in ArCF<sub>3</sub> offers an appealing strategy for rapid derivatization of ArCF<sub>3</sub>-containing drugs, and holds significant promise in drug discovery and modification. Following the success of two-component reactions for C(sp<sup>3</sup>)–F bond functionalization in ArCF<sub>3</sub>, preliminary studies have also been conducted on non-asymmetric three-component reactions. However, enantioselective three-component reactions <em>via</em> C(sp<sup>3</sup>)–F bond activation in ArCF<sub>3</sub> have not yet been developed. Herein, we report the first enantioselective three-component aryldifluoromethyl-alkynylation of alkenes through C(sp<sup>3</sup>)–F bond cleavage <em>via</em> dual photoredox/copper catalysis. This protocol is compatible with a wide array of trifluoromethylarenes bearing diverse substituents, various terminal alkynes and alkenes, enabling straightforward access to structurally diverse ArCF<sub>2</sub>-containing propargylic compounds in good yields with excellent enantioselectivities under mild conditions. Furthermore, the utility of this protocol was showcased through its application in the late-stage functionalization of a few drugs and bioactive molecular derivatives.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 3965-3975"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695859","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0