Organic chemistry frontiers : an international journal of organic chemistry最新文献_第3页

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

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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

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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

An efficient total synthesis of (+)-entecavir† （+）-恩替卡韦的高效全合成

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00329f

Chenlong Zhu , Nanlian Li , Yaopeng Ma , Bingfeng Sun

引用次数: 0

Bromotrifluoromethoxylation of allenes: expedient access to allylic trifluoromethoxy derivatives† 烯基溴三氟甲氧基化：丙烯基三氟甲氧基衍生物的一种权宜之计

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d4qo02426e

Rui Liu , Yangdong Hou , Pingping Tang

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Copper-mediated divergent synthesis of halogenated 1-pyrrolines, 3-azabicyclo[3.1.0]hex-2-enes and α,α-dibromo imines from N-allyl enamines† 铜介导N -烯丙基烯胺发散合成卤代1-吡咯、3-阿扎比环[3.1.0]己二烯和α， α-二溴亚胺

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00217f

Xiyan Duan , Junqi Wang , Kun Liu , Fengjiao Du , Maoling He , Wenxin Li , Xinming Liu , Pu Liu

{"title":"Copper-mediated divergent synthesis of halogenated 1-pyrrolines, 3-azabicyclo[3.1.0]hex-2-enes and α,α-dibromo imines from N-allyl enamines†","authors":"Xiyan Duan , Junqi Wang , Kun Liu , Fengjiao Du , Maoling He , Wenxin Li , Xinming Liu , Pu Liu","doi":"10.1039/d5qo00217f","DOIUrl":"10.1039/d5qo00217f","url":null,"abstract":"<div><div>By varying the halide type and its addition rate, the divergent synthesis of dibromo 1-pyrrolines, 3-azabicyclo[3.1.0]hex-2-enes, and α,α-dibromo imines from <em>N</em>-allyl enamines was successfully achieved. 1-Pyrrolines and 3-azabicyclo[3.1.0]hex-2-enes are important building blocks in organic synthesis and pharmaceutical chemistry. Herein, we disclose a chemodivergent protocol for the Cu-mediated, halide-controlled annulation of <em>N</em>-allyl enamines, enabling straightforward access to these valuable scaffolds with good yields and high selectivity. The type of halogen reagent, its addition rate, and the solvent are critical for controlling reaction selectivity. A reaction mechanism is proposed, which involves X-transfer/radical cyclization to construct pyrrolines or 3-azabicyclo[3.1.0]hex-2-enes. It is worth mentioning that <em>N</em>-allyl enamine serves as both a bromine acceptor and donor in this transformation. This strategy employs readily available starting materials, mild conditions, and a simple protocol and exhibits good functional group compatibility, demonstrating that <em>N</em>-allyl enamines are versatile building blocks for constructing nitrogen-containing heterocycles.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4012-4017"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734059","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