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How to Form Two Bonds in Three Ways: Reaction Trinity of σ,π-Heterosymmetric Diradicals. 如何以三种方式形成双键：σ、π-异对称双基的反应三位一体。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01539
Haonan Cheng,Yun Zeng,Xiaofan Zhang,Fangxu Pu,Aiguo Hu,Yun Ding
{"title":"How to Form Two Bonds in Three Ways: Reaction Trinity of σ,π-Heterosymmetric Diradicals.","authors":"Haonan Cheng,Yun Zeng,Xiaofan Zhang,Fangxu Pu,Aiguo Hu,Yun Ding","doi":"10.1021/acs.joc.5c01539","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01539","url":null,"abstract":"σ,π-Heterosymmetric diradicals are typically formed through the Myers-Saito cyclization of enyne-allene, featuring distinct chemical environments for the two radicals. In this study, maleic hydrazide was introduced at the ene position of enediyne molecules, leveraging the electron-withdrawing properties of these groups to facilitate the rearrangement of enediyne into enyne-allene, which subsequently leads to the generation of σ,π-heterosymmetric diradicals through cycloaromatization. Based on experimental results and computational analysis, we identified three competing reaction pathways for σ,π-heterosymmetric diradicals: (1) hydrogen atom abstraction by diradicals, (2) interactions of π-radicals with nucleophiles, and (3) interactions of σ-radicals with nucleophiles. In path 1, both radical centers can readily abstract hydrogens, with the σ-radical, showing a clear preference. In paths 2 and 3, the distortion of the core aromatic ring during the nucleophilic reaction leads to the disruption of the orthogonality of the radical orbitals through the formation of a Möbius-like conjugated framework, providing an efficient pathway for electron transfer and thereby facilitating both diradical quenching and nucleophilic addition.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"65 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145305428","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
Asymmetric Oxidative Coupling of 2-Naphthols Catalyzed by Chiral Copper–Amino Acid-Derived Ligand Complexes 手性铜-氨基酸配体络合物催化2-萘酚的不对称氧化偶联
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01655
Pei Tian, Mukeremu Aibibula, Xiangyu Sun, Yujie Wang, Tongtong Liu, Wenxuan Yu, Xiaohui Zhang, Xiaoyu Dong, Yan Xiong
{"title":"Asymmetric Oxidative Coupling of 2-Naphthols Catalyzed by Chiral Copper–Amino Acid-Derived Ligand Complexes","authors":"Pei Tian, Mukeremu Aibibula, Xiangyu Sun, Yujie Wang, Tongtong Liu, Wenxuan Yu, Xiaohui Zhang, Xiaoyu Dong, Yan Xiong","doi":"10.1021/acs.joc.5c01655","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01655","url":null,"abstract":"We developed a [Cu(CH<sub>3</sub>CN)<sub>4</sub>]<sup>+</sup>BF<sub>4</sub><sup>–</sup>/air-mediated asymmetric coupling method using novel <span>l</span>-amino acid-derived aminopyridine–amide ligands to access various <i>C</i><sub>2</sub>/<i>C</i><sub>1</sub>-symmetric BINOLs. This represents the first application of amide-containing ligands in copper-catalyzed asymmetric oxidative coupling of 2-naphthols. Notably, the efficient one-pot integration of the transesterification and coupling processes establishes a novel strategy for synthesizing ester-functionalized BINOLs. The formation of highly active Cu<sub>2</sub>O<sub>3</sub> oxides was detected from Cu(I) species under single-crystal X-ray diffraction analysis and is the key determinant for the stereoselective control of the catalytic cycle. Moreover, this method also enables the efficient synthesis of racemic binaphtholone compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"92 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145296014","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
Photochemical Ni-Catalyzed Selective Mono-N-Arylation 光化学镍催化选择性单- n -芳基化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c02127
Geyang Song, Ding-Zhan Nong, Gang Li, Juan Fan, Dong Xue
{"title":"Photochemical Ni-Catalyzed Selective Mono-N-Arylation","authors":"Geyang Song, Ding-Zhan Nong, Gang Li, Juan Fan, Dong Xue","doi":"10.1021/acs.joc.5c02127","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02127","url":null,"abstract":"The selective synthesis of <i>N</i>-monomethyl arylamines presents an important challenge in synthetic chemistry. Furthermore, small molecule amines readily coordinate with metal catalysts, causing catalyst deactivation. In this work, we report an efficient C–N coupling reaction of (hetero)aryl halides with small molecule amine salts. Without the need for an external photosensitizer in the presence of a soluble organic base, a bipyridine-Ni(II) complex serving as a catalyst successfully enables the selective C–N coupling of (hetero)aryl halides with methylamine, deuterated methylamine, ethylamine, and dimethylamine under purple light irradiation (390–395 nm), thus preventing catalyst deactivation. Mechanistic studies reveal that the reaction proceeds via a Ni(I)–Ni(III) catalytic cycle, and more than 100 examples showcase its feasibility and versatility in organic synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"77 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145306324","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
Palladium-Catalyzed Carbonylative Cross-Coupling of Aryl (Pseudo)halides and Cyclopropanols. 钯催化芳基（伪）卤化物与环丙醇羰基交叉偶联。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01963
Subramanian Srikriya,Pazhamalai Anbarasan
{"title":"Palladium-Catalyzed Carbonylative Cross-Coupling of Aryl (Pseudo)halides and Cyclopropanols.","authors":"Subramanian Srikriya,Pazhamalai Anbarasan","doi":"10.1021/acs.joc.5c01963","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01963","url":null,"abstract":"An efficient and general method for the synthesis of 1,4-diketones has been achieved through the palladium-catalyzed carbonylative cross-coupling of aryl halides with cyclopropanols. This methodology shows excellent compatibility with various functional groups and expands the scope for the synthesis of symmetrical and unsymmetrical 1,4-diketones with good efficiency. The synthetic utility of the diketones was demonstrated, and a plausible mechanism was also discussed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145305427","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
Correction to “Stereoselective Synthesis of Nucleotide Analog Prodrugs (ProTides) via an Oxazaphospholidine Method” 更正“用恶沙磷酸法立体选择性合成核苷酸类似前药（ProTides）”
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c02213
Monta Nakamura, Kiyoshi Kakuta, Kazuki Sato, Takeshi Wada
{"title":"Correction to “Stereoselective Synthesis of Nucleotide Analog Prodrugs (ProTides) via an Oxazaphospholidine Method”","authors":"Monta Nakamura, Kiyoshi Kakuta, Kazuki Sato, Takeshi Wada","doi":"10.1021/acs.joc.5c02213","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02213","url":null,"abstract":"Entries 1–3 and Entry 4 were conducted on 0.03 and 0.18 mmol scales, respectively. Entry 1: Determined from the <sup>31</sup>P NMR spectrum of crude mixture. Entries 2 and 3: Determined from the <sup>31</sup>P NMR spectra after purification. Entry 4 was determined from RP-HPLC after deprotection of the DMTr group of the model compound. All reagents were added as CH<sub>3</sub>CN solution. <b>(</b><i><b>S</b></i><b>p)-4b</b> and <b>(</b><i><b>R</b></i><b>p)-4b</b> were used in Entries 1–3 and Entry 4, respectively. Determined from the <sup>31</sup>P NMR spectra of crude mixtures. Determined from the <sup>31</sup>P NMR spectra of crude mixtures. Extraction in 0.2 M citric acid aqueous solution. Determined from the <sup>31</sup>P NMR spectra after purification. Determined from the <sup>31</sup>P NMR spectra of crude mixtures. Determined from the <sup>31</sup>P NMR spectra after purification. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.5c02213. Experimental details, HPLC profiles, copies of <sup>1</sup>H, <sup>13</sup>C, and <sup>31</sup>P NMR spectra of new compounds and final products (corrected) (PDF) Correction to “Stereoselective\u0000Synthesis of\u0000Nucleotide Analog Prodrugs (ProTides) via an Oxazaphospholidine Method” <span> 3 </span><span> views </span> <span> 0 </span><span> shares </span> <span> 0 </span><span> downloads </span> Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html. This article has not yet been cited by other publications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"198 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145306325","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
Synthetic Preparation of the Macrocyclolipopeptide Dysoxylactam A for Potent P-glycoprotein Inhibition. 有效抑制p糖蛋白的大环脂肽二羟内酰胺A的合成及制备。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01765
Petros Danielsen Siapkaras,Karoline Hanssen,Eirik Johansson Solum,Marius Aursnes
{"title":"Synthetic Preparation of the Macrocyclolipopeptide Dysoxylactam A for Potent P-glycoprotein Inhibition.","authors":"Petros Danielsen Siapkaras,Karoline Hanssen,Eirik Johansson Solum,Marius Aursnes","doi":"10.1021/acs.joc.5c01765","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01765","url":null,"abstract":"In 2019, the cyclolipopeptide dysoxylactam A was isolated and reported to be a potent inhibitor of the drug efflux pump P-glycoprotein and demonstrated the ability to reverse multidrug resistance in cancer cell lines. Herein, we report a reliable and flexible route toward dysoxylactam A, which features key transformations such as the Paterson 1,2-anti aldol reaction, an sp3-sp3 Fu-Suzuki coupling, asymmetric allylation, and the Corey-Nicolaou macrolactonization. All the data obtained on the synthesized natural product matched those of the authentic material.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"104 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145305429","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
Total Synthesis of Daphnepapytone A 全合成麻黄酮A
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01774
James B. Martinez, Paul R. Hanson
{"title":"Total Synthesis of Daphnepapytone A","authors":"James B. Martinez, Paul R. Hanson","doi":"10.1021/acs.joc.5c01774","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01774","url":null,"abstract":"The total synthesis of sesquiterpenoid daphnepapytone A starting from (<i>R</i>)-carvone is reported. The carbocyclic framework of daphnepapytone A was formed by a one-pot Pauson–Khand/desilylative oxidation reaction and a [2 + 2] photocycloaddition of synthetic oleodaphnone. During the synthesis, it was discovered that wavelength-dependent irradiation of oleodaphnone resulted in intramolecular photometathesis to form a dicyclopentadienone. Late-stage oxidation and a highly stereo- and regioselective reduction completed the synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"92 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145295778","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
PPh3-Promoted Sulfa-Michael Addition-Driven Cyclization: A Divergent Route to Access Spirothiochromanone Derivatives. pph3 -促进的磺胺-迈克尔加成驱动环化：获得螺酮衍生物的不同途径。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01450
Jyoti Chauhan,Jyoti Sikarwar,Rama Krishna Peddinti
{"title":"PPh3-Promoted Sulfa-Michael Addition-Driven Cyclization: A Divergent Route to Access Spirothiochromanone Derivatives.","authors":"Jyoti Chauhan,Jyoti Sikarwar,Rama Krishna Peddinti","doi":"10.1021/acs.joc.5c01450","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01450","url":null,"abstract":"A novel triphenylphosphine-mediated sulfa-Michael addition-triggered cascade reaction has been developed for the efficient synthesis of spirothiochromanone derivatives using 3H-benzo[c][1,2]dithiol-3-one as a sulfur surrogate. This transformation initiates with reductive S-S bond cleavage, smoothly delivering a diverse array of spiro-1,3-dimethylbarbiturate-thiochromanones and spiro-1,3-indanedione-thiochromanones under mild conditions. The current synthetic route features key advantages including operational simplicity, scalability, and excellent functional group compatibility with good to excellent conversions across substrates. Furthermore, this protocol obviates purification techniques such as column chromatography for the isolation of spiro-adducts, making it a valuable strategy for the construction of complex sulfur-containing spirocyclic scaffolds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145305430","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
Breaking Base Dependency: EDC·HCl-Promoted Henry Reaction under Solvent-Free Mild Acidic Conditions. 断碱依赖：EDC·hcl促进的亨利反应在无溶剂温和酸性条件下。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-15 DOI: 10.1021/acs.joc.5c01350
Prashant Shukla,Anurag Kumar Mishra,Mohammad Zahid Hussain,Ramalingam Peraman,Anupam Jana
{"title":"Breaking Base Dependency: EDC·HCl-Promoted Henry Reaction under Solvent-Free Mild Acidic Conditions.","authors":"Prashant Shukla,Anurag Kumar Mishra,Mohammad Zahid Hussain,Ramalingam Peraman,Anupam Jana","doi":"10.1021/acs.joc.5c01350","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01350","url":null,"abstract":"A sustainable, efficient, and scalable protocol for the Henry reaction between various aldehydes and nitroalkanes is presented, utilizing 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) as an organoacid. The reaction proceeds under solvent-free, room temperature conditions at acidic pH, delivering β-nitro alcohols in excellent yields of up to 99%. The methodology demonstrates a broad substrate scope, accommodating both electron-rich and electron-deficient aldehydes. Notably, the protocol operates under base-free conditions, suppresses elimination of byproducts, and is readily scalable to the gram level without loss in efficiency. These features make the process a valuable contribution to the green and practical pharmaceutical industry.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"102 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288527","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
Cobalt-Catalyzed Amide Bond Formation from Esters and Amines. 钴催化酯和胺形成酰胺键。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-15 DOI: 10.1021/acs.joc.5c01276
Xiao-Bin Li,Xiao-Xiong Lv,Fei Chen,Zhi-Hong Du,Chun-Bo Bo,Min Li,Donghui Wei,Ning Liu
{"title":"Cobalt-Catalyzed Amide Bond Formation from Esters and Amines.","authors":"Xiao-Bin Li,Xiao-Xiong Lv,Fei Chen,Zhi-Hong Du,Chun-Bo Bo,Min Li,Donghui Wei,Ning Liu","doi":"10.1021/acs.joc.5c01276","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01276","url":null,"abstract":"Amide bonds are ubiquitously present in natural products and drug molecules. Traditional methods for constructing amide bonds rely on stoichiometric activating reagents, often leading to the generation of substantial waste. Therefore, the development of green and sustainable synthetic approaches is of significant importance. This study reports a novel cobalt complex catalyst prepared by using inexpensive and readily available CoCl2 as a precursor, which efficiently promotes the amidation of esters with amines. Under optimized reaction conditions (toluene as the solvent, 15 mol % sodium tert-butoxide as the base, 0.6 mol % cobalt complex Cat-1 as the catalyst, 120 °C under a nitrogen atmosphere), the catalytic system exhibits high compatibility with various substituted methyl benzoates, heterocyclic esters, aromatic amines, and secondary amines, delivering products in 40%-85% yields. Notably, it also demonstrates minimal racemization toward chiral substrates with ee values maintained 85-99%. Furthermore, the method has been successfully applied to the synthesis of plant oil-based amide compounds and gram-scale reactions, highlighting its practical utility. This research provides an efficient and atom-economical new strategy for the green synthesis of amide bonds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288567","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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