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Unexpected Reaction of Dialkyl α-Hydroxy-benzylphosphonates with Dialkyl Phosphites and a Few Related Reactions 二烷基α-羟基苄基膦酸盐与二烷基亚磷酸盐的意外反应及一些相关反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02355
Zsuzsanna Szalai, Péter Ábrányi-Balogh, György Keglevich
{"title":"Unexpected Reaction of Dialkyl α-Hydroxy-benzylphosphonates with Dialkyl Phosphites and a Few Related Reactions","authors":"Zsuzsanna Szalai, Péter Ábrányi-Balogh, György Keglevich","doi":"10.1021/acs.joc.4c02355","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02355","url":null,"abstract":"The condensation of dialkyl α-hydroxy-benzylphosphonates with dialkyl phosphites and that of α-hydroxybenzyl-diphenylphosphine oxide with diphenylphosphine oxide unexpectedly gave the corresponding phosphorylated α-hydroxy derivatives. This new reaction proved to be general. The formation of the two products may be similar and involves the attack of the hydroxy group of the α-hydroxyphosphonate or α-hydroxyphosphine oxide on the phosphorus atom of the trivalent tautomer form (Y<sub>2</sub>POH) of the Y<sub>2</sub>P(O)H reagent (Y= MeO, EtO, or Ph) going with the elimination of an alcohol and water molecule, respectively. The mechanism was supported by DFT computations at the M062<i>X</i>/6-31G (d,p) level of theory, including suitable proton transfer networks. The condensations discussed are typical autocatalytic reactions promoted by the alcohol or water molecules formed. The initial promoters are the traces of water inevitably present in the mixture. In the reaction of α-hydroxyphosphonates with dialkyl phosphites, the −P(O)(OR)H derivative is the primary product that is partially hydrolyzed to the −P(O)(OH)H species by the traces of water under the conditions of the reaction. Arbuzov reaction of diethyl α-bromobenzylphosphonate with ethyl diphenyphosphinite afforded the target-like phenylmethylene-phosphine oxide─phosphonate derivative.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832800","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
Gold(I/III)-Catalyzed Sulfonylation of Aryl/Vinyl Iodides To Synthesize Aryl Sulfones 金（I/III）催化的芳基/乙烯基碘化物磺酰化反应合成芳基砜
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c01675
Lizhu Zhang, Wenqian Du, Jiawen Wu, Rongjie Yang, Fen Zhao, Baomin Fan, Zhonghua Xia
{"title":"Gold(I/III)-Catalyzed Sulfonylation of Aryl/Vinyl Iodides To Synthesize Aryl Sulfones","authors":"Lizhu Zhang, Wenqian Du, Jiawen Wu, Rongjie Yang, Fen Zhao, Baomin Fan, Zhonghua Xia","doi":"10.1021/acs.joc.4c01675","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01675","url":null,"abstract":"A gold-catalyzed sulfonylation of aryl/vinyl iodides to synthesize aryl sulfones facilitated by the ligand-enabled Au(I)/Au(III) redox catalysis was developed. In the reaction, aryl sodium sulfinates or sulphinic acids can react smoothly with aryl/vinyl iodides to directly construct various aryl sulfones. The strong synthetic capabilities of sulfone synthesis are demonstrated by its easily available and handled reagents, good functional group compatibility, and late-stage application of complicated biomolecules. Mechanistic studies suggest that the silver salt plays a crucial role in the transmetalation with the Au(I)/Au(III) intermediate, and the gold complex favors Au–S bond formation over Au–O bond formation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"87 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832798","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
α-Methylation Enables the X-ray Crystallographic Observation of Oligomeric Assemblies Formed by a β-Hairpin Peptide Derived from Aβ
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02344
Tuan D. Samdin, Adam G. Kreutzer, Victoria Sahrai, Michał Wierzbicki, James S. Nowick
{"title":"α-Methylation Enables the X-ray Crystallographic Observation of Oligomeric Assemblies Formed by a β-Hairpin Peptide Derived from Aβ","authors":"Tuan D. Samdin, Adam G. Kreutzer, Victoria Sahrai, Michał Wierzbicki, James S. Nowick","doi":"10.1021/acs.joc.4c02344","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02344","url":null,"abstract":"The assembly of the β-amyloid peptide Aβ into toxic oligomers plays a significant role in the neurodegeneration associated with the pathogenesis of Alzheimer’s disease. Our laboratory has developed <i>N</i>-methylation as a tool to enable X-ray crystallographic studies of oligomers formed by macrocyclic β-hairpin peptides derived from Aβ. In this investigation, we set out to determine whether α-methylation could be used as an alternative to <i>N</i>-methylation in studying the oligomerization of a β-hairpin peptide derived from Aβ. α-Methylation permits the crystallographic assembly of a triangular trimer and ball-shaped dodecamer, resembling assemblies formed by the <i>N</i>-methylated homolog. Subtle differences are observed in the conformation of the α-methylated peptide when compared to the <i>N</i>-methylated homolog. Notably, α-methylation appears to promote a flatter and more extended β-sheet conformation than that of <i>N</i>-methylated β-sheets or a typical unmodified β-sheet. α-Methylation provides an alternative to <i>N</i>-methylation in X-ray crystallographic studies of oligomers formed by peptides derived from Aβ, with the attractive feature of preserving NH hydrogen-bond donors along the peptide backbone.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832996","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
Hydrogenation of Sugar Enol-Ethers Using Pd/Et3SiH Reagent System: A Route to Deoxy Sugars/Glycosides 使用 Pd/Et3SiH 试剂系统氢化糖烯醚：脱氧糖/糖苷的途径
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02031
Bindu Tiwari, Ram Pratap Pandey, Nazar Hussain
{"title":"Hydrogenation of Sugar Enol-Ethers Using Pd/Et3SiH Reagent System: A Route to Deoxy Sugars/Glycosides","authors":"Bindu Tiwari, Ram Pratap Pandey, Nazar Hussain","doi":"10.1021/acs.joc.4c02031","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02031","url":null,"abstract":"We have developed a hydrogenation method using Pd(OAc)<sub>2</sub>/Et<sub>3</sub>SiH as a reagent system for sugar enol ethers and their glycosides. This approach is highly effective and applicable to a wide range of glycals and glycosides, achieving yields up to 96% for the corresponding deoxy sugars. Applying standard conditions to various O/C-glycosides resulted in excellent transformation to 2,3-dideoxy glycosides.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"247 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832801","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
Terpenylation of Ketones and a Secondary Alcohol under Hydrogen-Borrowing Manganese Catalysis 借氢锰催化下酮和仲醇的三戊基化反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02260
Sachin Jalwal, Sourajit Das, Subrata Chakraborty
{"title":"Terpenylation of Ketones and a Secondary Alcohol under Hydrogen-Borrowing Manganese Catalysis","authors":"Sachin Jalwal, Sourajit Das, Subrata Chakraborty","doi":"10.1021/acs.joc.4c02260","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02260","url":null,"abstract":"An Earth-abundant Mn–PNP pincer complex-catalyzed terpenylation of cyclic and acyclic ketones and secondary alcohol 1-phenylethanol using isoprenoid derivatives prenol, nerol, phytol, solanesol, and E-farnesol as allyl surrogates is reported. The C–C coupling reactions are green and atom-economic, proceeding via dehydrogenation of alcohols following a hydrogen autotransfer methodology aided by metal–ligand cooperation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"60 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832805","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
Elemental Sulfur/Selenium-Mediated Metal-Free Phosphinothioation and Phosphinoselenoation of Vinylsulfonium Salts with P–H Bonds 元素硫/硒介导的具有 P-H 键的乙烯基锍盐的无金属硫代磷酸化和硒代磷酸化反应
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02237
Biquan Xiong, Meng Li, Renfeng Cao, Sitong Yue, Weifeng Xu, Yu Liu, Longzhi Zhu, Ke-Wen Tang
{"title":"Elemental Sulfur/Selenium-Mediated Metal-Free Phosphinothioation and Phosphinoselenoation of Vinylsulfonium Salts with P–H Bonds","authors":"Biquan Xiong, Meng Li, Renfeng Cao, Sitong Yue, Weifeng Xu, Yu Liu, Longzhi Zhu, Ke-Wen Tang","doi":"10.1021/acs.joc.4c02237","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02237","url":null,"abstract":"An efficient and facile method has been developed for the construction of novel P–S–C and P–Se–C bonds by facilitating the three-component cross-coupling reaction of P–H bonds with elemental sulfur/selenium and vinylsulfonium salts, utilizing sodium bicarbonate as a base. This approach eliminates the need for the use of toxic and odorous active sulfur/selenium reagents and noble metals, thereby offering a new pathway for synthesizing <i>S</i>-phosphinothioates and <i>Se</i>-phosphinoselenoates via the organic conversion of inorganic sources. The reaction has showcased remarkable versatility in terms of substrate applicability, particularly for organophosphorus compounds containing P–H bonds and vinylsulfonium salt derivatives. The resulting phosphinothioation/phosphinoselenoation products can be obtained with high yield and regioselectivity. Additionally, a plausible reaction mechanism for this transformation has been proposed based on step-by-step control experiments and <sup>31</sup>P NMR tracking analysis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"63 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832804","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
Solvent Effects and Internal Functions Control Molecular Recognition of Neutral Substrates in Functionalized Self-Assembled Cages
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02190
Connor Z. Woods, Komal Sharma, Chengwei Chen, Lei Yang, Junyi Chen, Yu-Chen Wu, Naira S. Farooqi, Jingsong Zhang, Ryan R. Julian, Richard J. Hooley
{"title":"Solvent Effects and Internal Functions Control Molecular Recognition of Neutral Substrates in Functionalized Self-Assembled Cages","authors":"Connor Z. Woods, Komal Sharma, Chengwei Chen, Lei Yang, Junyi Chen, Yu-Chen Wu, Naira S. Farooqi, Jingsong Zhang, Ryan R. Julian, Richard J. Hooley","doi":"10.1021/acs.joc.4c02190","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02190","url":null,"abstract":"<b>A</b> suite of internally functionalized Fe<sub>4</sub>L<sub>6</sub> cage complexes has been synthesized with lipophilic end groups to allow dissolution in varied solvent mixtures, and the scope of their molecular recognition of a series of neutral, nonpolar guests has been analyzed. The lipophilic end groups confer cage solubility in solvents with a wide range of polarities, from hexafluoroisopropanol (HFIP) to tetrahydrofuran, and the hosts show micromolar affinities for neutral guests, despite having no flat panels enclosing the cavity. These hosts allow interrogation of the effects of an internal functional group on guest binding properties, as well as solvent-based driving forces for recognition. Introducing polar effects to the interior of the cavity enhances guest binding affinity in nonpolar solvents; adding space-filling aliphatic groups reduces affinity in all cases. While high dielectric solvents such as acetonitrile strongly favor guest binding, “low dielectric, high polarity” solvents such as HFIP strongly occupy the cavity and prevent guest recognition. Analysis of the cage optical transitions shows that the guests interact with the central ligand cores and reside in close proximity to the internal functions. These results have implications for supramolecular catalysis: balancing directed host:guest interactions (e.g., H-bonds) with entropic effects from solvent displacement is essential for reactions in these (and related) biomimetic hosts.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832803","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
A New Synthesis of Enantiopure Amine Fragment: An Important Intermediate to the Anti-HIV Drug Lenacapavir 对映体纯胺片段的新合成：抗艾滋病毒药物来那卡巴韦的重要中间体
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02380
Anand H. Shinde, Ramakrishna Sayini, Piyal Singh, Justina M. Burns, Saeed Ahmad, G. Michael Laidlaw, B. Frank Gupton, Douglas A. Klumpp, Limei Jin
{"title":"A New Synthesis of Enantiopure Amine Fragment: An Important Intermediate to the Anti-HIV Drug Lenacapavir","authors":"Anand H. Shinde, Ramakrishna Sayini, Piyal Singh, Justina M. Burns, Saeed Ahmad, G. Michael Laidlaw, B. Frank Gupton, Douglas A. Klumpp, Limei Jin","doi":"10.1021/acs.joc.4c02380","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02380","url":null,"abstract":"Herein, we describe a new seven-step approach to prepare (<i>S</i>)-1-(3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethan-1-amine ((<i>S</i>)-<b>4</b>) from the inexpensive 2-(3,5-difluorophenyl)acetic acid. The key steps in the sequence include (1) the Weinreb amide-based ketone synthesis to provide an entry point to the core structure; (2) simple functional group transformations to afford the racemic amine <b>4</b>-<i>rac</i>; and (3) dynamic kinetic resolution (DKR) to access the chiral amine (<i>S</i>)-<b>4</b>. This seven-step process delivered the enantiopure amine (<i>S</i>)-<b>4</b> in an overall isolated yield of approximately 15%. The process was demonstrated on a decagram scale, and the process requires no chromatographic purifications. Single-crystal X-ray crystallography measurements verified the chiral amine structure and absolute configuration.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832997","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
Zn(II)-Stabilized Azo-Anion Radical-Catalyzed Dehydrogenative Synthesis of Olefins
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02158
Subhasree Pal, Amit Kumar Guin, Subhankar Khanra, Nanda D. Paul
{"title":"Zn(II)-Stabilized Azo-Anion Radical-Catalyzed Dehydrogenative Synthesis of Olefins","authors":"Subhasree Pal, Amit Kumar Guin, Subhankar Khanra, Nanda D. Paul","doi":"10.1021/acs.joc.4c02158","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02158","url":null,"abstract":"Herein, we describe a Zn-catalyzed atom-economical, inexpensive, and sustainable method for preparing a broad spectrum of substituted olefins utilizing alcohols as the main precursor. Using a Zn(II) complex [ZnLCl<sub>2</sub>] (<b>1</b>) of the redox-noninnocent ligand 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (<b>L</b>), various (<i>E</i>)-olefins were prepared in good yields by coupling alcohols with sulfones and aryl cyanides under an inert atmosphere. Under an aerial atmosphere, vinyl nitriles were isolated in up to 82% yield reacting alcohols with benzyl cyanides in the presence of <b>1</b>. Control experiments and mechanistic investigation indicate the active involvement of the aryl-azo ligand as an electron and hydrogen reservoir, permitting <b>1</b> to perform as a promising catalyst.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"47 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832802","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
Pd-Catalyzed [2 + 2 + 2] Cyclization of Alkyne-cyclohexadienones and O-Akynyl Benzenesulfonamides for Construction of Fused Tricyclic Hydronaphthofurans 钯催化炔环己二烯酮和 O-炔基苯磺酰胺的[2 + 2 + 2]环化反应以构建融合三环萘并呋喃
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1021/acs.joc.4c02447
Miaomiao Tian, Xuxu Ma, Tianyun Zhang, Junbiao Chang, Bingxian Liu
{"title":"Pd-Catalyzed [2 + 2 + 2] Cyclization of Alkyne-cyclohexadienones and O-Akynyl Benzenesulfonamides for Construction of Fused Tricyclic Hydronaphthofurans","authors":"Miaomiao Tian, Xuxu Ma, Tianyun Zhang, Junbiao Chang, Bingxian Liu","doi":"10.1021/acs.joc.4c02447","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02447","url":null,"abstract":"A palladium-catalyzed [2 + 2 + 2] cyclization of 1,6-enynes with unsymmetrical alkynes has been successfully accomplished, resulting in the formation of a series of fused tricyclic hydronaphthofurans with high stereo- and regioselectivity in a single step. This reaction demonstrates 100% atomic economy and exhibits a broad substrate scope.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832730","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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