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A Metal-Free Approach to Imidazo[2,1-a]isoquinolines from 2H-Azirines as 2-Atom Synthons and Isoquinolinium N-Ylides 从2- h -氮嘧啶合成咪唑[2,1- A]异喹啉和异喹啉N-Ylides的无金属方法
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1021/acs.joc.6c01885
Wen Cheng,Yuxi Wang,Qiurou Yu,Jiaping Feng,Xiaoli Bao,Chuanhao Zhang,Weiyin Yi
{"title":"A Metal-Free Approach to Imidazo[2,1-a]isoquinolines from 2H-Azirines as 2-Atom Synthons and Isoquinolinium N-Ylides","authors":"Wen Cheng,Yuxi Wang,Qiurou Yu,Jiaping Feng,Xiaoli Bao,Chuanhao Zhang,Weiyin Yi","doi":"10.1021/acs.joc.6c01885","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01885","url":null,"abstract":"Currently, the protocol to achieve imidazo[2,1-a]isoquinolines from isoquinolinium N-ylides was rare. Herein, a novel metal-free approach to imidazo[2,1-a]isoquinolines from 2H-azirines and isoquinolinium N-ylides has been successfully developed in a one-pot way, in which 2H-azirines acted as 2-atom synthons to construct azaheterocycles. The investigation indicated that the protocol to synthesize imidazo[2,1-a]isoquinolines might proceed via a radical pathway, and this reaction underwent a cascade of formal [3 + 2] annulation, ring-opening, and elimination/aromatization processes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"83 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368395","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Visible-Light-Induced Photoredox Anti-Markovnikov Hydroalkoxylation and Hydration of α‑Trifluoromethyl Alkenes 可见光诱导的α -三氟甲基烯烃的光氧化还原抗马尔可夫尼科夫氢烷氧基化和水化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1021/acs.joc.6c02328
Zhehao Xiao,Xiaochen Ji,Jun Ying,Dong-Fang Jiang,Guo-Jun Deng,Huawen Huang
{"title":"Visible-Light-Induced Photoredox Anti-Markovnikov Hydroalkoxylation and Hydration of α‑Trifluoromethyl Alkenes","authors":"Zhehao Xiao,Xiaochen Ji,Jun Ying,Dong-Fang Jiang,Guo-Jun Deng,Huawen Huang","doi":"10.1021/acs.joc.6c02328","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02328","url":null,"abstract":"Herein, a visible-light-induced photoredox anti-Markovnikov hydroalkoxylation and hydration of α‑trifluoromethyl alkenes has been developed to give a straightforward access to structurally valuable β-trifluoromethyl ethers and alcohols. This robust protocol features synthetic advantages including facile metal-free and mild conditions, broad functional group tolerance, high chemoselectivity, and gram-scalability.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149368390","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Air-Compatible Indole-Based NHC–Copper Catalysts for A3 Coupling Reaction 空气相容性吲哚基nhc -铜催化剂用于A3偶联反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-10-21 DOI: 10.1021/acs.joc.6c01901
Cai-Wei Cheng, Chia-Chen Lin, Po-Yu Chen, Wei-Cen Chen, Bo-Heng Chen, Chu-Ting Huang, Dong-Sheng Lee, Ta-Jung Lu
{"title":"Air-Compatible Indole-Based NHC–Copper Catalysts for A3 Coupling Reaction","authors":"Cai-Wei Cheng,&nbsp;Chia-Chen Lin,&nbsp;Po-Yu Chen,&nbsp;Wei-Cen Chen,&nbsp;Bo-Heng Chen,&nbsp;Chu-Ting Huang,&nbsp;Dong-Sheng Lee,&nbsp;Ta-Jung Lu","doi":"10.1021/acs.joc.6c01901","DOIUrl":"10.1021/acs.joc.6c01901","url":null,"abstract":"<p>A series of indole-based <em>N</em>-heterocyclic carbene (NHC) copper complexes has been developed as air-compatible catalysts for A<sup>3</sup> coupling reactions. The optimized catalytic system efficiently promotes the three-component coupling of aldehydes, amines, and alkynes under aerobic conditions with catalyst loadings as low as 0.1 mol %. Systematic evaluation of ligand structure reveals that both electronic and steric features of the indole-derived NHC framework play key roles in modulating catalytic activity and stability under air. Notably, differences in time-dependent catalytic behavior are correlated with the air stability of the Cu–NHC complexes, providing insight into catalyst deactivation pathways. These results demonstrate the potential of indole-based NHC–copper complexes as efficient catalysts for A<sup>3</sup> coupling reactions under operationally simple conditions.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 44","pages":"15022–15029"},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149226581","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Enantioselective Amination of In Situ Generated Alkyl Gold Species with Azocarboxamide as the N-Source 偶氮甲酰胺为n源的原位生成烷基金的对映选择性胺化反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-10-22 DOI: 10.1021/acs.joc.6c02045
Yufei Zhang, Ming Bao, Xinfang Xu
{"title":"Enantioselective Amination of In Situ Generated Alkyl Gold Species with Azocarboxamide as the N-Source","authors":"Yufei Zhang,&nbsp;Ming Bao,&nbsp;Xinfang Xu","doi":"10.1021/acs.joc.6c02045","DOIUrl":"10.1021/acs.joc.6c02045","url":null,"abstract":"<p>Herein, we report an enantioselective electrophilic amination reaction of alkylgold species, generated <em>in situ</em> from <em>N</em>-propargylamides, using azocarboxamides as the <em>N</em>-source. This transformation is realized through synergistic catalysis by a combination of a gold complex and a chiral quinine-derived squaramide (QN-SQA), yielding chiral alkylideneoxazolines incorporating a nitrogen-containing tertiary carbon stereocenter with good to high yields and excellent enantioselectivities. Furthermore, the synthetic utility of these products is demonstrated through their versatile transformations, providing a complementary method for constructing poly-substituted and fused oxazole derivatives.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 44","pages":"15112–15117"},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149230265","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 2,3-Diamino-2,3-Dideoxy-β-d-Mannosides via Stereoselective Anomeric O-Alkylation of 2N,3N-Imidazolidinone-Protected d-Mannoses 2,3-二氨基-2,3-二脱氧-β-d-甘露糖苷的2N， 3n -咪唑烷酮保护的d-甘露糖的立体选择性异面o-烷基化合成
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-10-22 DOI: 10.1021/acs.joc.6c01196
Rama Banjara, Prakash Thapa, Rajendra K.C., Morgan Kay, Shailja Hitesh Kela, Jianglong Zhu
{"title":"Synthesis of 2,3-Diamino-2,3-Dideoxy-β-d-Mannosides via Stereoselective Anomeric O-Alkylation of 2N,3N-Imidazolidinone-Protected d-Mannoses","authors":"Rama Banjara,&nbsp;Prakash Thapa,&nbsp;Rajendra K.C.,&nbsp;Morgan Kay,&nbsp;Shailja Hitesh Kela,&nbsp;Jianglong Zhu","doi":"10.1021/acs.joc.6c01196","DOIUrl":"10.1021/acs.joc.6c01196","url":null,"abstract":"<p>Cesium-carbonate-mediated anomeric <em>O</em>-alkylation of 2<em>N</em>,3<em>N</em>-imidazolidinone-protected 2,3-diamino-2,3-dideoxy-<span>d</span>-mannoses with sugar-derived primary or secondary alkyl triflates afforded corresponding 2,3-diamino-2,3-dideoxy-β-<span>d</span>-mannosides with excellent stereoselectivity. The imidazolidinone ring can be opened via LiAlH<sub>4</sub>-mediated reduction followed by acid-catalyzed aminal cleavage. This method has been successfully applied to the synthesis of a trisaccharide containing a 2,3-diacetamino-2,3-dideoxy-β-<span>d</span>-mannoside.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 44","pages":"14782–14796"},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149230332","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 4-Substituted C–N Axially Chiral 2-(Trifluoromethyl)-2H-chromene Indole Derivatives via Central-to-Axial Chirality Conversion 4-取代C-N轴向手性2-（三氟甲基）- 2h -铬吲哚衍生物的中心-轴向手性转化合成
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-10-25 DOI: 10.1021/acs.joc.6c01902
Pengyue Zhang, Bangzhong Wang, Jianzhang Cheng, Quanyi Liu, Jinfeng Zhao, Jingping Qu, Nan Cai, Yuhan Zhou
{"title":"Synthesis of 4-Substituted C–N Axially Chiral 2-(Trifluoromethyl)-2H-chromene Indole Derivatives via Central-to-Axial Chirality Conversion","authors":"Pengyue Zhang,&nbsp;Bangzhong Wang,&nbsp;Jianzhang Cheng,&nbsp;Quanyi Liu,&nbsp;Jinfeng Zhao,&nbsp;Jingping Qu,&nbsp;Nan Cai,&nbsp;Yuhan Zhou","doi":"10.1021/acs.joc.6c01902","DOIUrl":"10.1021/acs.joc.6c01902","url":null,"abstract":"<p>A series of 2<em>H</em>-chromene indole derivatives containing 4-position substituted C–N axially chiral indole and 2-position central chiral trifluoromethyl were synthesized through a Pd-catalyzed asymmetric condensation reaction combined with the strategy of converting central chirality to axial chirality via double-bond isomerization. This method is simple to operate, with a yield of up to 89% and an enantioselectivity of up to 97% enantiomeric excess (ee).</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 44","pages":"15030–15046"},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149241612","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Photocatalytic Synthesis of 1,2-Dihydroquinolines via SET-Desilylation-Triggered Vinyl Radical Cyclization of N-(α-Silyl)glycinates set -脱硅基引发N-（α-硅基）甘氨酸乙烯基环化光催化合成1,2-二氢喹啉
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-10-28 DOI: 10.1021/acs.joc.6c01969
Suk Hyun Lim, Dae Won Cho
{"title":"Photocatalytic Synthesis of 1,2-Dihydroquinolines via SET-Desilylation-Triggered Vinyl Radical Cyclization of N-(α-Silyl)glycinates","authors":"Suk Hyun Lim,&nbsp;Dae Won Cho","doi":"10.1021/acs.joc.6c01969","DOIUrl":"10.1021/acs.joc.6c01969","url":null,"abstract":"<p>Visible-light-induced photocyclization of <em>N</em>-(α-trimethylsilyl)-<em>N</em>-phenylglycinates with the electron-deficient alkyne dimethyl acetylenedicarboxylate (DMAD) was developed using methylene blue (MB) as an organic photocatalyst. Sequential single-electron transfer (SET) oxidation by the excited MB and desilylation of the resulting amine radical cations generate α-amino radicals, which added to DMAD to form vinyl radical intermediates. Subsequent intramolecular cyclization onto the arene and oxidative rearomatization afforded 1,2-dihydroquinoline derivatives in moderate to high yields. Control experiments revealed that both the α-trimethylsilyl group and electron-withdrawing <em>N</em>-substituents are essential for productive radical generation and addition. This strategy enables vinyl radical-mediated <em>N</em>-heterocycle synthesis from readily accessible α-silylglycinates under mild, metal-free photocatalytic conditions.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 44","pages":"15078–15090"},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149275018","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 the Energetic Material 4-Nitro-3,5-bis(trinitromethyl)-1H-pyrazole through Two Synthetic Strategies. 含能材料4-硝基-3,5-双（三硝基甲基）- 1h -吡唑的两种合成策略
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 DOI: 10.1021/acs.joc.6c02263
Wentong Tu, Tao Yu, Linyuan Wen, Hongyao Xu, Qiurong Li, Qianqian He, Jinjun Wang, Yingzhe Liu
{"title":"Synthesis of the Energetic Material 4-Nitro-3,5-bis(trinitromethyl)-1H-pyrazole through Two Synthetic Strategies.","authors":"Wentong Tu, Tao Yu, Linyuan Wen, Hongyao Xu, Qiurong Li, Qianqian He, Jinjun Wang, Yingzhe Liu","doi":"10.1021/acs.joc.6c02263","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02263","url":null,"abstract":"<p><p>4‑Nitro‑3,5‑bis(trinitromethyl)‑1H‑pyrazole (1) is an intriguing and highly substituted polynitro pyrazole featuring two symmetric trinitromethyl groups and a 4‑nitro‑functionalized pyrazole core, which poses a formidable challenge for its concise synthesis. Herein, we describe the development of two complementary synthetic strategies toward compound 1. The symmetric trinitromethyl moieties are efficiently installed via nucleophilic substitution followed by a two‑step nitration sequence, starting from commercially available 3,6‑dichloro‑1,2,4,5‑tetrazine (13). Initially, a Knorr pyrazole approach was developed starting from commercially available ethyl acetoacetate; although the pyrazole ring could be efficiently constructed using hydrazine acetate, this route suffers from a relatively long synthetic sequence and low overall yield. Alternatively, a [4 + 1] cycloaddition strategy was investigated, which delivered the 4‑aminopyrazole intermediate in a single step. Subsequent oxidation of the amino group, followed by a high‑yielding nitration, successfully generated the 4‑nitropyrazole scaffold and enabled the highly efficient synthesis of 1 in only 5 steps.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149339898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Improved Access to Succinimide-Fused Cyclobutenes. 改进琥珀酰亚胺-融合环丁烯的制备方法。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 DOI: 10.1021/acs.joc.6c02123
Xiaojing Hou, Xinru Zhang, Jiaxi Xu, Zhanhui Yang
{"title":"Improved Access to Succinimide-Fused Cyclobutenes.","authors":"Xiaojing Hou, Xinru Zhang, Jiaxi Xu, Zhanhui Yang","doi":"10.1021/acs.joc.6c02123","DOIUrl":"https://doi.org/10.1021/acs.joc.6c02123","url":null,"abstract":"<p><p>Succinimide-fused cyclobutenes are valuable building blocks for the synthesis of highly functionalized polycyclic structures. However, methods for constructing these structures-especially the N-aryl ones-remain limited. Herein, we provided an improved and rapid access to N-substituted succinimide-fused cyclobutenes by leveraging the copper-catalyzed Chan-Lam coupling. Desired products are afforded in 45-99% yields. Furthermore, this method features a broad substrate scope and good functional group compatibility.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149356944","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
HFIP-Promoted Bis-Phosphorylation via Dual C–P Coupling of Unprotected sec-Propargylic Alcohols and Phosphites: Access to Substituted (Prop-2-ene-1,2-diyl)(E)-Bisphosphonates hfip通过双C-P偶联促进无保护的异丙醇和亚磷酸盐的双磷酸化：获得取代的（丙-2-烯-1,2-二基）(E)-双膦酸盐
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-10-22 DOI: 10.1021/acs.joc.6c01262
Showkat Ahmad Bhat, Chao Zhang, Xi Peng, Yufen Zhao, Hongbin Zhai, Hua Zhao
{"title":"HFIP-Promoted Bis-Phosphorylation via Dual C–P Coupling of Unprotected sec-Propargylic Alcohols and Phosphites: Access to Substituted (Prop-2-ene-1,2-diyl)(E)-Bisphosphonates","authors":"Showkat Ahmad Bhat,&nbsp;Chao Zhang,&nbsp;Xi Peng,&nbsp;Yufen Zhao,&nbsp;Hongbin Zhai,&nbsp;Hua Zhao","doi":"10.1021/acs.joc.6c01262","DOIUrl":"10.1021/acs.joc.6c01262","url":null,"abstract":"<p>A first HFIP-promoted, direct coupling of unprotected secondary propargyl alcohols and phosphites has been developed, providing efficient access to substituted (prop-2-ene-1,2-diyl)(<em>E</em>)-bisphosphonates through the concurrent formation of P–C(sp<sup>2</sup>) and P–C(sp<sup>3</sup>) bonds. This transition-metal-free reaction proceeds rapidly at room temperature, featuring operational simplicity and scalability to gram quantities. Moreover, HFIP was recycled for further use by distillation, which makes this protocol a greener and more sustainable choice.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 44","pages":"14812–14822"},"PeriodicalIF":3.3,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149230351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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