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Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C–N Coupling
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.4c04582
Joseph Hatton, David R. Stuart
{"title":"Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C–N Coupling","authors":"Joseph Hatton, David R. Stuart","doi":"10.1021/acs.orglett.4c04582","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04582","url":null,"abstract":"Modular C–N coupling is a desirable way to construct <i>N</i>-aryl carbamates, which are privileged scaffolds in active pharmaceutical ingredients. However, there are no broadly applicable metal-free methods for the<i>N</i>-arylation of carbamates. Herein, we describe a metal-free approach that uses aryl(TMP)iodonium salts as arylation reagents for cyclic carbamates by exploiting the metal-like reactivity of iodine(III). The scope includes 25 examples, including 17 different aryl(TMP)iodonium salts and 9 different carbamates, in yields ranging between 55 and 97% (75% avg).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"8 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030892","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
Acid-Promoted Phosphorylation of Ynones for the Synthesis of Phosphoryl Enones
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04531
Xiao-Hong Wei, Ya-Wen Xue, Xiu-Mei Jiang, Gang-Gui Quan, Jia-Qiang Ye, Xu Guo, Xuan Liu
{"title":"Acid-Promoted Phosphorylation of Ynones for the Synthesis of Phosphoryl Enones","authors":"Xiao-Hong Wei, Ya-Wen Xue, Xiu-Mei Jiang, Gang-Gui Quan, Jia-Qiang Ye, Xu Guo, Xuan Liu","doi":"10.1021/acs.orglett.4c04531","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04531","url":null,"abstract":"An efficient phospha-aldol/Meyer-Schuster rearrangement cascade reaction between propargylic aldehydes and phosphine oxides has been developed in which various phosphoryl enones were obtained in moderate to excellent yields. A comprehensive series of mechanistic experiments, including the identification of key intermediates and the application of <sup>18</sup>O isotope labeling, has confirmed that this cascade reaction proceeds through a phospha-aldol followed by Meyer–Schuster rearrangement cascade reaction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"51 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027001","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
Unveiling Heavier Dihydropyridine Chalcogenol Esters in Metallaphotoredox Catalyst-Enabled Regioselective Hydrothio(seleno)carbonylation
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04577
Amit Pal, Sandip Bag, Sariga Mangalamundackal Vijayan, Anshuman Bera, Sivaranjana Reddy Vennapusa, Basudev Sahoo
{"title":"Unveiling Heavier Dihydropyridine Chalcogenol Esters in Metallaphotoredox Catalyst-Enabled Regioselective Hydrothio(seleno)carbonylation","authors":"Amit Pal, Sandip Bag, Sariga Mangalamundackal Vijayan, Anshuman Bera, Sivaranjana Reddy Vennapusa, Basudev Sahoo","doi":"10.1021/acs.orglett.4c04577","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04577","url":null,"abstract":"Herein, aromaticity-driven thio(seleno)ester group transfer from novel 1,4-dihydropyridine thio(seleno)esters to alkene feedstocks is disclosed by merging palladium and photoredox catalysis. In this process, photoactivation of dihydropyridine thio(seleno)esters is integrated with regioselective hydrometalation of alkenes, avoiding photoinduced Pd–C bond homolysis of organopalladium intermediates. Additionally, a regioselective hydroselenocarbonylation of an alkene is accomplished for the first time using a bench-stable selenoester reagent. The activation mode of novel dihydropyridine thioesters has been illustrated by detailed mechanistic studies, spectroscopic analysis, intermediate trapping, and isotope labeling experiments.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"49 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027012","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
Chiral Phosphoric Acid-Catalyzed Asymmetric Synthesis of Axially Chiral Arylpyrazole 手性磷酸催化不对称合成轴手性芳基吡唑
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c03996
Shujun Tong, Jiaqi Pu, Yu Qi, Shi-Wu Li
{"title":"Chiral Phosphoric Acid-Catalyzed Asymmetric Synthesis of Axially Chiral Arylpyrazole","authors":"Shujun Tong, Jiaqi Pu, Yu Qi, Shi-Wu Li","doi":"10.1021/acs.orglett.4c03996","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03996","url":null,"abstract":"A chiral phosphoric acid-catalyzed efficient, operationally simple, general method for straightforward syntheses of axially chiral arylpyrazole employing <i>N</i>-alkyl of 3-aryl-5-aminopyrazoles reacting with azonaphthalenes was achieved. A wide variety of axially chiral heterobiaryl diamines in generally good yields with excellent enantioselectivities were obtained under mild conditions. In addition, a scaled-up experiment and postmodification of the chiral product further highlighted the synthetic utility.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"626 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143021132","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
Shining a Light on Peptide and Protein Synthesis: Light-Emitting-Diode-Driven Desulfurization of Cysteine to Alanine with Rose Bengal
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04671
Mateusz Waliczek, Piotr Stefanowicz
{"title":"Shining a Light on Peptide and Protein Synthesis: Light-Emitting-Diode-Driven Desulfurization of Cysteine to Alanine with Rose Bengal","authors":"Mateusz Waliczek, Piotr Stefanowicz","doi":"10.1021/acs.orglett.4c04671","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04671","url":null,"abstract":"Studies presenting visible-light-induced desulfurization of peptides containing a cysteine residue have been carried out. This transformation driven by light-emitting-diode-type light proceeds with high efficiency in an aqueous solution at room temperature and involves the use of a catalytic amount of photosensitizer, Rose Bengal. The procedure has been tested on model synthetic peptides, lysozyme C and α-crystallin, and successfully applied to a one-pot native chemical ligation (NCL)–desulfurization protocol.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"74 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027002","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
Ortho-Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04564
Yuxuan Xu, Runmei Li, Fengjun Liang, Xiaolong Peng, Yahu A. Liu, Fei Jia, Ke Wen
{"title":"Ortho-Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents","authors":"Yuxuan Xu, Runmei Li, Fengjun Liang, Xiaolong Peng, Yahu A. Liu, Fei Jia, Ke Wen","doi":"10.1021/acs.orglett.4c04564","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04564","url":null,"abstract":"<i>Ortho</i>-functionalization of pillar[<i>n</i>]arenes has been a formidable challenge, partially due to the fragility of their macrocyclic skeletons. In this concise report, we describe a facile synthetic method for monoarylation/alkylation at the position <i>ortho</i> to the oxime functionality in pillar[4]arene[1]benzoquinone monoxime (<b>1</b>) via addition of Grignard reagents. The described method enables the creation of various mono-<i>ortho</i>-alkyl/aryl-substituted pillar[5]arene derivatives that were previously inaccessible.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"58 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027011","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
Thianthrenium-Enabled Chromium-Catalyzed Deuterated Alkyl Addition to Aldehydes via a Photoactive Electron Donor–Acceptor Complex 通过光活性电子供体-受体配合物，镧使铬催化氘化烷基加成到醛
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04516
Wenjuan Xiao, Youye Tian, Liting Du, Wen Liu, Changping Fang, Mengtao Ma, Binlin Zhao
{"title":"Thianthrenium-Enabled Chromium-Catalyzed Deuterated Alkyl Addition to Aldehydes via a Photoactive Electron Donor–Acceptor Complex","authors":"Wenjuan Xiao, Youye Tian, Liting Du, Wen Liu, Changping Fang, Mengtao Ma, Binlin Zhao","doi":"10.1021/acs.orglett.4c04516","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04516","url":null,"abstract":"The Nozaki–Hiyama–Kishi reaction offers effective and reliable strategies for the preparation of alcohols via carbon–carbon bond formation. Typical methods usually require stoichiometric amounts of chromium salts, co-transition metals, and auxiliary reagents, which limits their practical application in industrial chemistry. To mitigate these limitations, substantial efforts have been made to develop chromium-catalytic approaches. However, an excess of metal reductants or expensive photocatalysts played essential roles during the catalytic cycles. Here, we present a photoactive electron donor–acceptor (EDA) complex-induced chromium-catalyzed route, accomplishing alkyl addition to aldehydes without the requirement of metal reductants or photocatalysts. Furthermore, on the basis of the pH-dependent site-selective hydrogen isotope exchange of alkyl thianthrenium salts, a range of β-deuterated secondary alcohols could be prepared with high efficiency and excellent deuterium incorporation. Mechanistic studies revealed that the photoinduced intramolecular single-electron transfer of the EDA complex happened to provide alkyl radicals that are captured by Cr(II) species to facilitate the subsequent carbon–carbon bond formation. Meanwhile, the excited Hantzsch ester could act as a terminal reductant for the turnover of the chromium catalyst.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143020938","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
Nickel-Catalyzed Three-Component Carboamination/Cyclization of Alkynes To Access 2,3-Disubstituted Quinolines
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04753
Yang Gao, Jiale Xing, Yanping Huo, Qian Chen, Xianwei Li, A. Stephen K. Hashmi, Zhongyi Zeng
{"title":"Nickel-Catalyzed Three-Component Carboamination/Cyclization of Alkynes To Access 2,3-Disubstituted Quinolines","authors":"Yang Gao, Jiale Xing, Yanping Huo, Qian Chen, Xianwei Li, A. Stephen K. Hashmi, Zhongyi Zeng","doi":"10.1021/acs.orglett.4c04753","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04753","url":null,"abstract":"Presented herein is a nickel-catalyzed chemo- and regioselective three-component tandem carboamination and cyclization of terminal alkynes with organoboronic acids and anthranils for facile and modular access to 2,3-substituted quinolines. In this process, anthranil has dual roles: serving as an electrophilic aminating reagent and a redox buffer to suppress the generation of an off-cycle Ni(0) complex. Moreover, the anionic acetylacetonate (acac) ligand was found to be vital to ensure a productive Ni(I)–Ni(III)–Ni(I) catalytic cycle.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027003","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
N-Phenylphenothiazine-based Hyper-cross-linked Polymers for Recyclable, Heterogeneous Photocatalysis of Organic Transformations: A Strategy to Access 6-Difluoromethyl-phenanthridines
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04585
Shengjie Song, Wenjian Wang, Yali He, Xiaoye Cheng, Zhi Chen, Jiadi Zhou, Jianjun Li
{"title":"N-Phenylphenothiazine-based Hyper-cross-linked Polymers for Recyclable, Heterogeneous Photocatalysis of Organic Transformations: A Strategy to Access 6-Difluoromethyl-phenanthridines","authors":"Shengjie Song, Wenjian Wang, Yali He, Xiaoye Cheng, Zhi Chen, Jiadi Zhou, Jianjun Li","doi":"10.1021/acs.orglett.4c04585","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04585","url":null,"abstract":"Herein, a <i>N</i>-phenylphenothiazine-based hyper-cross-linked polymer (PTH-HCP) was finely designed and constructed, which serves as a metal-free heterogeneous photocatalyst for organic transformations. Characterization experiments have shown that this polymer demonstrates outstanding stability, extensive surface area, and exceptional photoelectric response properties. Moreover, PTH-HCP showed good catalytic efficiency and recyclability in the photochemically driven difluoromethylation/cyclization reactions. This work provides a strategy for the design and construction of polymer photocatalysts and offers support for their broad prospects in synthetic applications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027013","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
A Stereoselective Oxidative Dimerization En Route to (−)-Lomaiviticin A 合成(−)-洛马维汀A的立体选择性氧化二聚化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-23 DOI: 10.1021/acs.orglett.4c04098
Mikaela DiBello, Zhi Xu, Alexandria M. Palazzo, Seth B. Herzon
{"title":"A Stereoselective Oxidative Dimerization En Route to (−)-Lomaiviticin A","authors":"Mikaela DiBello, Zhi Xu, Alexandria M. Palazzo, Seth B. Herzon","doi":"10.1021/acs.orglett.4c04098","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04098","url":null,"abstract":"We describe a stereoselective synthesis of the dimeric diazofluorene <b>15</b>, a potential precursor to the cytotoxic <i>C</i><sub>2</sub>-symmetric bacterial metabolite (−)-lomaiviticin A (<b>1</b>). An efficient route was developed to convert the tetracyclic diol <b>5</b> to the diketone <b>4</b> (five steps, 30% overall). Oxidative dimerization of the enoxysilane <b>14</b> provided the <i>C</i><sub>2</sub>-symmetric dimeric diazofluorene <b>15</b> in 56% yield and with 15:1:0 diastereoselectivity. Deprotection and 2D NMR analysis indicated that the major diastereomer possessed the (2<i>S</i>,2′<i>S</i>) configuration found in <b>1</b>. This approach may ultimately be useful in the synthesis of <b>1</b> itself.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143021131","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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