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Phosphorus Catalysis Enabling α-sp3-C-H Amination of 2-Alkylpyridines 磷催化使2-烷基吡啶α-sp3-C-H胺化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-19 DOI: 10.1039/d5qo00960j
Yoshito Heike, Asa Tagata, Akira Yada, Kanako Nozawa-Kumada, Masaya Sawamura, Yohei Shimizu
{"title":"Phosphorus Catalysis Enabling α-sp3-C-H Amination of 2-Alkylpyridines","authors":"Yoshito Heike, Asa Tagata, Akira Yada, Kanako Nozawa-Kumada, Masaya Sawamura, Yohei Shimizu","doi":"10.1039/d5qo00960j","DOIUrl":"https://doi.org/10.1039/d5qo00960j","url":null,"abstract":"Phosphorus-catalyzed sp3-C-H amination of 2-alkylpyridines was developed as a notable advancement of a catalytic sp3-C-H functionalization by an organophosphorus compound. Racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) acted as a particularly efficient catalyst precursor for the reaction of 2-alkylpyridines with dibutyl azodicarboxylate (DBAD) as an aminating agent in the presence of water and cesium carbonate as promoters in dichloromethane as a critical solvent, allowing the sp 3 -C-H amination under mild reaction conditions at 0 °C. The reaction proceeded exclusively at the C(α)position even in the presence of more acidic C-H bonds. A quaternary azaphosphonium cation, generated by the reaction between BINAP and DBAD followed by solvolytic N-chloromethylation, is proposed to be the active catalyst that reacts directly with the alkylpyridine substrate.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"24 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144664599","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
Exploring the intricacies of inverse hydride shuttle catalysis in azabicyclic scaffold construction with contiguous stereocenters 探索具有连续立体中心的氮杂环支架结构中反氢化物穿梭催化的复杂性
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-18 DOI: 10.1039/d5qo00627a
Damanpreet Kaur, Saurabh Vinod Parmar, Aniket Nigade, Vidya Avasare
{"title":"Exploring the intricacies of inverse hydride shuttle catalysis in azabicyclic scaffold construction with contiguous stereocenters","authors":"Damanpreet Kaur, Saurabh Vinod Parmar, Aniket Nigade, Vidya Avasare","doi":"10.1039/d5qo00627a","DOIUrl":"https://doi.org/10.1039/d5qo00627a","url":null,"abstract":"Asymmetric catalysis is crucial for synthetic organic chemistry, with significant implications in the synthesis of natural products and pharmaceuticals. Despite experimental advancements in the synthesis of chiral azabicyclic scaffolds using achiral organocatalysts and fluoro-aryl boranes, the fundamental mechanistic origins behind the introduction of three contiguous stereocenters remain largely unexplored. This study presents the first computational investigation into the intricacies of inverse hydride shuttle catalysis and the effect of electron-withdrawing groups in the asymmetric synthesis of azabicyclic frameworks. The condensed Fukui function analysis was employed to unravel the structure–activity relationship of five different fluoro-aryl boranes in the asymmetric synthesis of alkaloid scaffolds. The activation strain model analysis provided a quantitative assessment of contributions from interactions and deformations. The insights discovered align with experimental observations and could prove valuable in establishing efficient, selective, and sustainable methods for stereoselective synthesis without the need for any chiral source in the reaction.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"677 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144652624","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
Inorganic Reagents in photochemical Reactions 光化学反应中的无机试剂
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-18 DOI: 10.1039/d5qo00888c
Zhan-Yong Wang, Ziyan Zhang, Yang Liu, Yumeng Li, Xinyue Dong, Ran Xia
{"title":"Inorganic Reagents in photochemical Reactions","authors":"Zhan-Yong Wang, Ziyan Zhang, Yang Liu, Yumeng Li, Xinyue Dong, Ran Xia","doi":"10.1039/d5qo00888c","DOIUrl":"https://doi.org/10.1039/d5qo00888c","url":null,"abstract":"Inorganic reagents are safe, low-cost, easy to store, and easy to remove after a reaction. These properties make them attractive for direct use in organic synthesis. Inorganic reagents can serve as radical initiators, H/D sources, nucleophiles, radical precursors, C1 synthons, S sources and oxidizing agents in organic photochemical reactions under mild and environmentally friendly conditions. Key inorganic reagents discussed include HCO2Na/K, NaH2PO2, CF3SO2Na, HCF2SO2Na, RSO2Na, EtO2CCO2K, CO, CO2, NH3, NH4OAc, NaN3, Cu(NO3)2, H2O, D2O, O2 (or air), AgSCF3, MSCN/MSeCN (M=Na, K, NH4), K2S, S8, Se, Na2S2O5, K2S2O5, NaCl, KCl, MgCl2, KBr and KHF2. This review highlights the benefits of combining inorganic reagents with organic photochemical reactions, such as low cost, safety, and simplicity, in line with green chemistry principles.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144652661","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
Construction of Fused BN-Heterocycles via Boron Atom Insertion: DFT Insights into the Lewis Acid-Base (BBr3/NEt3) Cooperative Mechanism and Selectivity 通过硼原子插入构建融合bn -杂环：对Lewis酸碱（BBr3/NEt3）协同机制和选择性的DFT洞察
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-16 DOI: 10.1039/d5qo00870k
Jingxin Hu, Lin Zhang, Zexing Cao
{"title":"Construction of Fused BN-Heterocycles via Boron Atom Insertion: DFT Insights into the Lewis Acid-Base (BBr3/NEt3) Cooperative Mechanism and Selectivity","authors":"Jingxin Hu, Lin Zhang, Zexing Cao","doi":"10.1039/d5qo00870k","DOIUrl":"https://doi.org/10.1039/d5qo00870k","url":null,"abstract":"The BBr3-mediated N-heterocycle editing reaction through boron atom insertion strategy reported by Song et al. (Angew. Chem., Int. Ed. 2024, 63, e202318613), has been systematically explored by density functional theory (DFT) calculations. The present results reveal that, in addition to BBr3 acting as a boron source and nucleophile, the Lewis base NEt3 also plays a crucial role. Specifically, the Lewis acid-base cooperative interaction between BBr3 and NEt3 facilitates the ring-opening of the substrate 1-(2-vinylphenyl) azetidine, the rate-determining step of the overall cascade reaction. Notably, the organic base NEt3 facilitates the formation of the real nucleophilic species BBr4⁻, thereby promoting the progression of the reaction. Furthermore, the formation of an exceptionally stable C4NB π-ring intermediate and the difference in distortion and exchange-repulsion energies, caused by substrate structural characteristics, are responsible for chemoselectivity and regioselectivity of substrates bearing typical structural motifs and functional groups, respectively. These computational findings not only provide profound mechanistic insights into the tandem reactions involved in the construction of fused BN‐heterocycles, but also elucidate the underlying factors governing substrate preference.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"74 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144640529","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
Combined Photoredox and Carbene Catalysis: Alkene Borocarbonylation via the Persistent Radical Effect 联合光氧化还原和碳烯催化：通过持续自由基效应的烯烃硼羰基化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-16 DOI: 10.1039/d5qo00819k
Xiaochen Wang, Senhui Wu, Hongyu Zhang, Qingmin Wang, Shu-Rong Ban
{"title":"Combined Photoredox and Carbene Catalysis: Alkene Borocarbonylation via the Persistent Radical Effect","authors":"Xiaochen Wang, Senhui Wu, Hongyu Zhang, Qingmin Wang, Shu-Rong Ban","doi":"10.1039/d5qo00819k","DOIUrl":"https://doi.org/10.1039/d5qo00819k","url":null,"abstract":"Herein, we report a mild and operationally simple dual-catalytic method for the synthesis of <em>β</em>-boryl carbonyl compounds via alkene difunctionalization. Specifically, combining <em>N</em>-heterocyclic carbene catalysis and photocatalysis enables a three-component radical cross-coupling reaction between a wide range of feedstock carboxylic acids, easily prepared NHC-boranes, and readily available alkenes to yield structurally diverse <em>β</em>-boryl carbonyl compounds. Longer lifetime ketyl radicals facilitate efficient boron participation in the coupling through the persistent radical effect. The method could be used to install acyl and borane groups on highly functionalized natural-product-derived compounds without pre–activation in one step and most products show good diastereoselectivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"51 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144640530","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
Terpene cyclization catalysis with a functional cavitand: driving selectivity through precise molecular recognition 用功能空腔催化萜烯环化：通过精确分子识别驱动选择性
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-15 DOI: 10.1039/d5qo00922g
Ricard López-Coll, Agustí Lledó
{"title":"Terpene cyclization catalysis with a functional cavitand: driving selectivity through precise molecular recognition","authors":"Ricard López-Coll, Agustí Lledó","doi":"10.1039/d5qo00922g","DOIUrl":"https://doi.org/10.1039/d5qo00922g","url":null,"abstract":"A three-walled self-folding cavitand receptor derived from resorcin[4]arene featuring phenol groups near the confined space catalyzes the cyclization reaction of nerol, using HCl as co-catalyst. In contrast to terpene cyclization reactions mediated by other synthetic hosts, the process reported herein is substrate specific, provides very high selectivity towards cyclization products, and delivers limonene—a thermodynamically disfavored product—as the major compound. The observed acceleration, turnover and unique selectivity are rationalized on the basis of precise molecular recognition phenomena, supported by NMR studies and DFT calculations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"13 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144640531","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
Photoredox/Cobalt Dual-Catalyzed Regioselective Hydroalkoxylation of 1,3-Dienes with Alcohols 光氧化还原/钴双催化1,3-二烯与醇的区域选择性氢烷氧基化
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-15 DOI: 10.1039/d5qo00777a
Bei Chen, Zhimeng Song, Yukun Chen, Xingru Yan, Ge Zhang, Qian Zhang
{"title":"Photoredox/Cobalt Dual-Catalyzed Regioselective Hydroalkoxylation of 1,3-Dienes with Alcohols","authors":"Bei Chen, Zhimeng Song, Yukun Chen, Xingru Yan, Ge Zhang, Qian Zhang","doi":"10.1039/d5qo00777a","DOIUrl":"https://doi.org/10.1039/d5qo00777a","url":null,"abstract":"Catalytic hydroalkoxylation of alkenes with oxygen-nucleophiles is of great interest and importance but remains an under developing task in synthetic chemistry. Here, we developed a photoredox and Co-catalyzed regioselective hydroalkoxylation of 1,3-dienes with alcohols, which enables efficient access to valuable allylic ethers in good to excellent yields. The reaction features mild conditions, good functional group tolerance, and wide substrate scope. Application of this rection to late-stage functionalization of relatively complex natural products and bioactive molecules further increases the utility of the developed methodology. Mechanistic studies suggest that the reaction underwent a CoH-mediated hydrogen atom transfer (HAT) to 1,3-diene, followed by a radical-polar crossover process involving nucleophilic displacement of allylic cobalt(IV) with free alcohols. This reaction is an important complement to the arsenal of transition-metal-catalyzed hydroalkoxylation of alkenes, providing a new strategy to deliver valuable allylic ethers.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"7 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144630219","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
Lumiflavine-Catalyzed, Visible-Light-Driven Allylation of Cyclobutanone Oximes: A Sustainable Approach to Distally Unsaturated Nitriles 荧光黄催化的可见光驱动环丁酮肟烯丙基化：远端不饱和腈的可持续途径
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-15 DOI: 10.1039/d5qo00695c
Yanyu Lu, Kaiyu Yan, Yanzhe Shi, Cuiqing Gao, Yitao Zhu, Yinlei Zhang, Teck Peng Loh, Peizhong Xie
{"title":"Lumiflavine-Catalyzed, Visible-Light-Driven Allylation of Cyclobutanone Oximes: A Sustainable Approach to Distally Unsaturated Nitriles","authors":"Yanyu Lu, Kaiyu Yan, Yanzhe Shi, Cuiqing Gao, Yitao Zhu, Yinlei Zhang, Teck Peng Loh, Peizhong Xie","doi":"10.1039/d5qo00695c","DOIUrl":"https://doi.org/10.1039/d5qo00695c","url":null,"abstract":"We present a naturally derived organophotoredox catalyst system for the ring-opening allylation of cyclobutanone O-acetyl oxime esters. This metal-free process operates under mild and environmentally benign conditions, demonstrating broad substrate compatibility. A range of distally unsaturated nitriles were synthesized in good to excellent yields with high stereoselectivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"109 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144630139","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
One-Pot Cobalt-Catalyzed Ring-Opening of Diaziridines for Bismuth-Promoted Fischer Indole Synthesis 铋促进Fischer吲哚合成中钴催化双氮嘧啶开环的一锅反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-15 DOI: 10.1039/d5qo00802f
Xiao-Lei Zhang, Le Wang, Cheng-Long Wang, Shen-Yuan Zhang, Zi-Hao Li, Shuyu Zhang, Heyuan Bai
{"title":"One-Pot Cobalt-Catalyzed Ring-Opening of Diaziridines for Bismuth-Promoted Fischer Indole Synthesis","authors":"Xiao-Lei Zhang, Le Wang, Cheng-Long Wang, Shen-Yuan Zhang, Zi-Hao Li, Shuyu Zhang, Heyuan Bai","doi":"10.1039/d5qo00802f","DOIUrl":"https://doi.org/10.1039/d5qo00802f","url":null,"abstract":"Indole serves as a privileged scaffold in numerous natural products and pharmaceuticals, with Fischer indole synthesis representing the most widely employed synthetic methodology. In this study, we introduce a cobalt-catalyzed, one-pot strategy for bismuth-promoted Fischer indole synthesis via ring-opening of diaziridines. This approach circumvents the use of toxic linear hydrazines and enables the synthesis of diverse indole derivatives under mild conditions with inexpensive reagents, offering a green and practical method for Fischer indole synthesis.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"671 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144630218","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
Metal- and Base-Free Spirocyclization of Alkylidene Oxindoles via Photo- and Mechanochemically Generated Nitrile Ylides and Nitrile Imines as 1, 3-Dipoles 光化学和机械化学合成的腈酰亚胺和腈亚胺作为1,3偶极子的烷基二烯氧吲哚的金属和无碱螺旋环化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-07-15 DOI: 10.1039/d5qo00851d
Shweta Singh, Roopam Pandey, Varun Christopher, Mahesh Kumar Ravva, Rakesh Ganguly, Subhabrata Sen
{"title":"Metal- and Base-Free Spirocyclization of Alkylidene Oxindoles via Photo- and Mechanochemically Generated Nitrile Ylides and Nitrile Imines as 1, 3-Dipoles","authors":"Shweta Singh, Roopam Pandey, Varun Christopher, Mahesh Kumar Ravva, Rakesh Ganguly, Subhabrata Sen","doi":"10.1039/d5qo00851d","DOIUrl":"https://doi.org/10.1039/d5qo00851d","url":null,"abstract":"Herein we have reported an expedient synthesis of spiro[pyrrolidine-3, 3′-oxindole] and 2'-aryl-2',4'-dihydrospiro[indoline-3,3'-pyrazol]-2-one under metal and base free conditions through the 3+2 cycloaddition reactions of in situ generated nitrile ylides and nitrile imines with alkylidene oxindoles in good to excellent yield. The nitrile ylides are generated through acetonitrile insertion onto carbenes generated from blue LED irradiation of aryl diazo esters. The nitrile imines were formed under mechanochemical condition from diazo esters and aryl diazonium tetrafluoroborates.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"99 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144630116","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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