ACS Organic & Inorganic Au最新文献

{"title":"Synthesis of Indolyl Phenyl Diketones through Visible-Light-Promoted Ni-Catalyzed Intramolecular Cyclization/Oxidation Sequence of Ynones","authors":"Yufeng Zhou,&nbsp;Yaping Wang,&nbsp;Peidong Xu,&nbsp;Weiwei Han,&nbsp;Heng-Ying Xiong* and Guangwu Zhang*,&nbsp;","doi":"10.1021/acsorginorgau.3c00060","DOIUrl":"10.1021/acsorginorgau.3c00060","url":null,"abstract":"<p >The combination of visible light catalysis and Ni catalysis has enabled the synthesis of indolyl phenyl diketones through the cyclization/oxidation process of ynones. This reaction proceeded under mild and base-free conditions and showed a broad scope and feasibility for gram-scale synthesis. Several natural products and biologically interesting molecules could be readily postfunctionalized by this method.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 2","pages":"241–247"},"PeriodicalIF":0.0,"publicationDate":"2023-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00060","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138951228","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Expedient Azide–Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO4 with Cu(0) in Aqueous Media","authors":"Wen-Chieh Yang,&nbsp; and ,&nbsp;Chien-Tien Chen*,&nbsp;","doi":"10.1021/acsorginorgau.3c00059","DOIUrl":"10.1021/acsorginorgau.3c00059","url":null,"abstract":"<p >A series of vanadium(III), vanadyl(IV/V) species, inorganic metal oxides, and transition-metal oxides was examined as cocatalysts with Cu(0) powder for copper(I)-catalyzed azide-alkyne cycloaddition. Among them, vanadyl(IV) species bearing acetylacetonate, acetate, and sulfate, vanadyl(V) isopropoxide, and vanadate were suitable for the click reactions of per-acetyl and per-benzyl β-azido glycosides with three different terminal alkynes in CH₃CN. Water-soluble vanadyl(IV) sulfate was further selected for efficient click reactions for unprotected β-glycosyl azides and even compatible with a thiol-containing substrate in aqueous media at ambient temperature.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 2","pages":"235–240"},"PeriodicalIF":0.0,"publicationDate":"2023-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00059","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138743458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Quadrupolar, Highly Polarized Dyes: Emission Dependence on Viscosity and Selective Mitochondria Staining","authors":"Mariusz Tasior,&nbsp;Olena Vakuliuk,&nbsp;Antoni Wrzosek,&nbsp;Valentine I. Vullev*,&nbsp;Adam Szewczyk*,&nbsp;Denis Jacquemin* and Daniel T. Gryko*,&nbsp;","doi":"10.1021/acsorginorgau.3c00035","DOIUrl":"10.1021/acsorginorgau.3c00035","url":null,"abstract":"<p >Quadrupolar A-D-A-type 1,4-dihydropyrrolo[3,2-<i>b</i>]pyrroles (DHPPs) bearing pyridinium and quinolinium substituents emit in the 500–600 nm region. The enhancement of electronic communication between the electron-rich heterocyclic core and electron-deficient peripheral substituents turned out to be crucial for achieving emission enhancement in viscous media. DHPP bearing two 4-pyridinium substituents has optical brightness 34,000 in glycerol and only 700 in MeOH, as evidenced by measurements of the emission intensity and fluorescence lifetimes in a series of polar solvents. Such behavior makes it an excellent candidate for viscosity probes in fluorescence microscopy, as demonstrated by the fluorescence imaging of H9C2 cardiomyocytes.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 2","pages":"248–257"},"PeriodicalIF":0.0,"publicationDate":"2023-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00035","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138680902","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synergistic Merger of Ketone, Halogen Atom Transfer (XAT), and Nickel-Mediated C(sp3)–C(sp2) Cross-Electrophile Coupling Enabled by Light","authors":"Alisha Rani Tripathy,&nbsp;Akash Bisoyi,&nbsp;Arya P,&nbsp;Sreelakshmi Venugopal and Veera Reddy Yatham*,&nbsp;","doi":"10.1021/acsorginorgau.3c00062","DOIUrl":"10.1021/acsorginorgau.3c00062","url":null,"abstract":"<p >In the present manuscript, we have developed a unique catalytic system by merging photoexcited ketone catalysis, halogen atom transfer (XAT), and nickel catalysis to forge C(sp³)–C(sp²) cross-electrophile coupling products from unactivated iodoalkanes and (hetero)aryl bromides. The synergistic catalytic system works under mild reaction conditions and tolerates a variety of functional groups; moreover, this strategy allows the late-stage modification of medicinally relevant molecules. Preliminary mechanistic studies reveal the role of the α-aminoalkyl radical, which further participates in the XAT process with alkyl iodides to generate the desired alkyl radical, which eventually intercepts with the nickel catalytic cycle to liberate the products in good to excellent yields.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 2","pages":"229–234"},"PeriodicalIF":0.0,"publicationDate":"2023-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00062","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138680971","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Redox-Neutral Decarboxylative Cross-Coupling of Oxamates with Aryl Bromides","authors":"Akash Bisoyi,&nbsp;Vijay Kumar Simhadri,&nbsp;Surya K,&nbsp;Rositha Kuniyil* and Veera Reddy Yatham*,&nbsp;","doi":"10.1021/acsorginorgau.3c00053","DOIUrl":"10.1021/acsorginorgau.3c00053","url":null,"abstract":"<p >Dual nickel-photoredox-enabled direct synthesis of amides through cross-coupling of cesium oxamates with aryl bromides has been developed. This methodology’s key advantages are mild reaction conditions, utilizing organic dye as a photocatalyst, employing readily available starting chemicals as coupling partners, and late-stage carbamoylation of pharmaceutically relevant molecules. DFT studies suggested that the nickel catalytic cycle proceeds via a radical addition pathway prior to the oxidative insertion.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 2","pages":"223–228"},"PeriodicalIF":0.0,"publicationDate":"2023-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00053","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138507606","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Advanced Electroanalysis for Electrosynthesis","authors":"Monica Brachi,&nbsp;Wassim El Housseini,&nbsp;Kevin Beaver,&nbsp;Rohit Jadhav,&nbsp;Ashwini Dantanarayana,&nbsp;Dylan G. Boucher and Shelley D. Minteer*,&nbsp;","doi":"10.1021/acsorginorgau.3c00051","DOIUrl":"10.1021/acsorginorgau.3c00051","url":null,"abstract":"<p >Electrosynthesis is a popular, environmentally friendly substitute for conventional organic methods. It involves using charge transfer to stimulate chemical reactions through the application of a potential or current between two electrodes. In addition to electrode materials and the type of reactor employed, the strategies for controlling potential and current have an impact on the yields, product distribution, and reaction mechanism. In this Review, recent advances related to electroanalysis applied in electrosynthesis were discussed. The first part of this study acts as a guide that emphasizes the foundations of electrosynthesis. These essentials include instrumentation, electrode selection, cell design, and electrosynthesis methodologies. Then, advances in electroanalytical techniques applied in organic, enzymatic, and microbial electrosynthesis are illustrated with specific cases studied in recent literature. To conclude, a discussion of future possibilities that intend to advance the academic and industrial areas is presented.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 2","pages":"141–187"},"PeriodicalIF":0.0,"publicationDate":"2023-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00051","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138507620","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Modeling of Optical Band-Gap Values of Mixed Oxides Having Spinel Structure AB2O4 (A = Mg, Zn and B = Al, Ga) by a Semiempirical Approach","authors":"Francesco Di Quarto*,&nbsp;Andrea Zaffora,&nbsp;Francesco Di Franco and Monica Santamaria,&nbsp;","doi":"10.1021/acsorginorgau.3c00030","DOIUrl":"10.1021/acsorginorgau.3c00030","url":null,"abstract":"<p >Spinel oxides with the general formula AB₂O₄ comprise a large family of compounds covering a very wide range of band-gap values (1 eV &lt; <i>E</i>_g &lt; 8 eV) as a function of the nature of the metallic cations A and B. Owing to this, the physical properties of these materials have been largely exploited both from a fundamental point of view, for their variable electronic properties, and for their possible use in numerous engineering applications. Herein, the modeling of ZnAl₂O₄, ZnGa₂O₄, MgAl₂O₄, and MgGa₂O₄ cubic spinel oxides has been carried out by using the semiempirical approach based on the difference of electronegativity between oxygen and the average electronegativity of cations present in the oxides. The results of recent theoretical extensions of our semiempirical approach to ternary and quaternary oxides have been tested for spinel oxides with metallic ions occupying both octahedrally and tetrahedrally coordinated sites in different ratios. A detailed analysis of the experimental band-gap values and comparison with the theoretically estimated values has been carried out for ternary ZnAl₂O₄, ZnGa₂O₄, MgAl₂O₄, and MgGa₂O₄ spinels as well as for double spinels Mg(Al_2<i>x</i>Ga_2–<i>x</i>)O₄ and Zn(Al_2<i>x</i>Ga_2–<i>x</i>)O₄, and quaternary mixed oxides (Zn_<i>x</i>Mg_{(1–<i>x</i>)})Al₂O₄ and (Zn_<i>x</i>Mg_{(1–<i>x</i>)})Ga₂O₄. The wide range of band-gap values reported in the literature for simple or double spinels has been related to the different preparation methods affecting the grain dimension of crystalline spinel samples as well as to the presence of crystallographic defects and/or impurities in the spinel matrix. The good agreement between experimental band-gap values and the theoretical ones strongly supports the use of our semiempirical approach in the area of band-gap engineering of new materials.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 1","pages":"120–134"},"PeriodicalIF":0.0,"publicationDate":"2023-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00030","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138507607","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A Celebration of the Publication of the 100th Volume of Organic Syntheses","authors":"Margaret M. Faul*,&nbsp; and ,&nbsp;Kay M. Brummond*,&nbsp;","doi":"10.1021/acsorginorgau.3c00057","DOIUrl":"https://doi.org/10.1021/acsorginorgau.3c00057","url":null,"abstract":"","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"3 6","pages":"328–331"},"PeriodicalIF":0.0,"publicationDate":"2023-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00057","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138489492","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Bifunctional MOFs in Heterogeneous Catalysis","authors":"Srinivasan Natarajan*,&nbsp; and ,&nbsp;Krishna Manna,&nbsp;","doi":"10.1021/acsorginorgau.3c00033","DOIUrl":"10.1021/acsorginorgau.3c00033","url":null,"abstract":"<p >The ever-increasing landscape of heterogeneous catalysis, pure and applied, utilizes many different catalysts. Academic insights along with many industrial adaptations paved the way for the growth. In designing a catalyst, it is desirable to have <i>a priori</i> knowledge of what structure needs to be targeted to help in achieving the goal. When focusing on catalysis, one needs to cope with a vast corpus of knowledge and information. The overwhelming desire to exploit catalysis toward commercial ends is irresistible. In today’s world, one of the requirements of developing a new catalyst is to address the environmental concerns. The well-established heterogeneous catalysts have microporous structures (&lt;25 Å), which find use in many industrial processes. The metal–organic framework (MOF) compounds, being pursued vigorously during the last two decades, have similar microporosity with well-defined pores and channels. The MOFs possess large surface area and assemble to delicate structural and compositional variations either during the preparation or through postsynthetic modifications (PSMs). The MOFs, in fact, offer excellent scope as simple Lewis acidic, Brönsted acidic, Lewis basic, and more importantly bifunctional (acidic as well as basic) agents for carrying out catalysis. The many advances that happened over the years in biology helped in the design of many good biocatalysts. The tools and techniques (advanced preparative approaches coupled with computational insights), on the other hand, have helped in generating interesting and good inorganic catalysts. In this review, the recent advances in bifunctional catalysis employing MOFs are presented. In doing so, we have concentrated on the developments that happened during the past decade or so.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 1","pages":"59–90"},"PeriodicalIF":0.0,"publicationDate":"2023-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00033","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135042010","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Friedel–Crafts-Type Arylation Strategy for the Conversion of Alkyl 2-((Diphenoxyphosphoryl)oxy)-2-arylacetates to α,α-Diaryl Esters","authors":"Kauê C. Capellaro,&nbsp;Tales A. C. Goulart,&nbsp;Rafael D. C. Gallo,&nbsp;Juliana de S. Schenfel and Igor D. Jurberg*,&nbsp;","doi":"10.1021/acsorginorgau.3c00042","DOIUrl":"10.1021/acsorginorgau.3c00042","url":null,"abstract":"<p >An arylation strategy allowing the conversion of alkyl 2-((diphenoxyphosphoryl)oxy)-2-arylacetates to α,α-diaryl esters is reported. This transformation can be promoted by TfOH when the starting organic phosphates do not carry <i>para</i>-alkoxy groups on their aryl rings, but it does not require any additives when such groups are present. These alkyl 2-((diphenoxyphosphoryl)oxy)-2-arylacetates can be readily accessed from the insertion of diphenyl phosphate into aryldiazoacetates.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 1","pages":"106–112"},"PeriodicalIF":0.0,"publicationDate":"2023-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00042","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135291065","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}