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Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins. 氟化酸功能化富电子镍卟啉的合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-15 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.248
Mike Brockmann, Jonas Lobbel, Lara Unterriker, Rainer Herges
{"title":"Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins.","authors":"Mike Brockmann, Jonas Lobbel, Lara Unterriker, Rainer Herges","doi":"10.3762/bjoc.20.248","DOIUrl":"10.3762/bjoc.20.248","url":null,"abstract":"<p><p>In this study, novel fluorinated carboxylic acid esters of the generic structure TfO-CH<sub>2</sub>-(CF<sub>2</sub>) <i><sub>n</sub></i> -COOCH<sub>3</sub> (<i>n</i> = 2,4,6, Tf = triflate) were synthesized. The triflates were reacted with 2-hydroxy-3,4,5-trimethoxybenzaldehyde via Williamson ether syntheses. The resulting electron-rich compounds were used as aldehydes in the Rothemund reaction with pyrrole to form ester-substituted porphyrins. After metalation with Ni(acac)<sub>2</sub> and hydrolysis electron-rich porphyrins were obtained, that are equipped with covalently attached long chain acid substituents. The target compounds have potential applications in catalysis, sensing, and materials science. The fluorinated aliphatic carboxylic acids (TfO-CH<sub>2</sub>-(CF<sub>2</sub>) <i><sub>n</sub></i> -COOCH<sub>3</sub>) with triflate as leaving group in terminal position are easily accessible and versatile building blocks for attaching long chain acids (p<i>K</i> <sub>a</sub> 0-1) to substrates in Williamson ether-type reactions.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2954-2958"},"PeriodicalIF":2.2,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11572008/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides. gem-二氟乙烯基和三氟乙烯基迈克尔受体在合成α，β-不饱和含氟和非含氟酰胺中的应用。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-15 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.247
Monika Bilska-Markowska, Marcin Kaźmierczak, Wojciech Jankowski, Marcin Hoffmann
{"title":"<i>gem</i>-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides.","authors":"Monika Bilska-Markowska, Marcin Kaźmierczak, Wojciech Jankowski, Marcin Hoffmann","doi":"10.3762/bjoc.20.247","DOIUrl":"10.3762/bjoc.20.247","url":null,"abstract":"<p><p>The incorporation of fluorine atoms within the structure of organic compounds is known to exert a significant impact on their electronic properties, thereby modulating their reactivity in diverse chemical transformations. In the context of our investigation, we observed a striking illustration of this phenomenon. A Michael addition involving <i>gem</i>-difluorovinyl and trifluorovinyl acceptors was successfully achieved, demonstrating high stereoselectivity. This selectivity was further elucidated through theoretical calculations. Using this methodology, a series of new α,β-unsaturated amides, both fluorinated and nonfluorinated, were synthesized.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2946-2953"},"PeriodicalIF":2.2,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11572014/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667102","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
4,6-Diaryl-5,5-difluoro-1,3-dioxanes as chiral dopants for liquid crystal compositions. 4,6-二芳基-5,5-二氟-1,3-二氧杂环作为液晶组合物的手性掺杂剂。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-14 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.246
Maurice Médebielle, Peer Kirsch, Jérémy Merad, Carolina von Essen, Clemens Kühn, Andreas Ruhl
{"title":"4,6-Diaryl-5,5-difluoro-1,3-dioxanes as chiral dopants for liquid crystal compositions.","authors":"Maurice Médebielle, Peer Kirsch, Jérémy Merad, Carolina von Essen, Clemens Kühn, Andreas Ruhl","doi":"10.3762/bjoc.20.246","DOIUrl":"10.3762/bjoc.20.246","url":null,"abstract":"<p><p>Two racemic <i>anti</i>-4,6-diphenyl-5,5-difluoro-1,3-dioxanes were prepared and the corresponding enantiomers were evaluated as potential new chiral dopants for liquid-crystal compositions.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2940-2945"},"PeriodicalIF":2.2,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11572010/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667105","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Structure and thermal stability of phosphorus-iodonium ylids. 磷-碘鎓亚基的结构和热稳定性。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-14 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.245
Andrew Greener, Stephen P Argent, Coby J Clarke, Miriam L O'Duill
{"title":"Structure and thermal stability of phosphorus-iodonium ylids.","authors":"Andrew Greener, Stephen P Argent, Coby J Clarke, Miriam L O'Duill","doi":"10.3762/bjoc.20.245","DOIUrl":"10.3762/bjoc.20.245","url":null,"abstract":"<p><p>Hypervalent iodine(III) reagents have become indispensable tools in organic synthesis, but gaps remain in the functionalities they can transfer. In this study, a fundamental understanding of the thermal stability of phosphorus-iodonium ylids is obtained through X-ray diffraction, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Insights into the structural factors affecting thermal stability and potential decomposition pathways will enable the future design and development of new reagents.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2931-2939"},"PeriodicalIF":2.2,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11571945/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667133","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts. 涉及超价碘盐的无过渡金属芳基化反应的最新进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-13 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.243
Ritu Mamgain, Kokila Sakthivel, Fateh V Singh
{"title":"Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts.","authors":"Ritu Mamgain, Kokila Sakthivel, Fateh V Singh","doi":"10.3762/bjoc.20.243","DOIUrl":"10.3762/bjoc.20.243","url":null,"abstract":"<p><p>Diaryliodonium salts have become widely recognized as arylating agents in the last two decades. Both, symmetrical and unsymmetrical forms of these salts serve as effective electrophilic arylating reagents in various organic syntheses. The use of diaryliodoniums in C-C and carbon-heteroatom bond formations, particularly under metal-free conditions, has further enhanced the popularity of these reagents. In this review, we concentrate on various arylation reactions involving carbon and other heteroatoms, encompassing rearrangement reactions in the absence of any metal catalyst, and summarize advancements made in the last five years.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2891-2920"},"PeriodicalIF":2.2,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11572100/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667118","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives. 二氰亚甲基功能化紫罗兰酮衍生物的电荷传输特性。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-13 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.244
Sondos A J Almahmoud, Joseph Cameron, Dylan Wilkinson, Michele Cariello, Claire Wilson, Alan A Wiles, Peter J Skabara, Graeme Cooke
{"title":"The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives.","authors":"Sondos A J Almahmoud, Joseph Cameron, Dylan Wilkinson, Michele Cariello, Claire Wilson, Alan A Wiles, Peter J Skabara, Graeme Cooke","doi":"10.3762/bjoc.20.244","DOIUrl":"10.3762/bjoc.20.244","url":null,"abstract":"<p><p>The study of organic small molecule semiconductor materials as active components of organic electronic devices continues to attract considerable attention due to the range of advantages these molecules can offer. Here, we report the synthesis of three dicyanomethylene-functionalised violanthrone derivatives (<b>3a</b>, <b>3b</b> and <b>3c</b>) featuring different alkyl substituents. It is found that the introduction of the electron-deficient dicyanomethylene groups significantly improves the optical absorption compared to their previously reported precursors <b>2a</b>-<b>c</b>. All compounds are p-type semiconductors with low HOMO-LUMO gaps (≈1.25 eV). The hole mobilities, measured from fabricated organic field-effect transistors, range from 3.6 × 10<sup>-6</sup> to 1.0 × 10<sup>-2</sup> cm<sup>2</sup> V<sup>-1</sup> s<sup>-1</sup>. We found that the compounds featuring linear alkyl chains (<b>3b</b> and <b>3c</b>) displayed a higher mobility compared to the one with branched alkyl chains, <b>3a</b>. This could be the result of the more highly disordered packing arrangement of this molecule in the solid state, induced by the branched side chains that hinder the formation of π-π stacking interactions. The influence of dicyanomethylene groups on the charge transport properties was most clearly observed in compound <b>3b</b> which has a 60-fold improvement in mobility compared to <b>2b</b>. This study demonstrates that the choice of the solubilising group has a profound effect on the hole mobility on these organic semiconductors.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2921-2930"},"PeriodicalIF":2.2,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11572013/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667125","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
C-H Trifluoromethylthiolation of aldehyde hydrazones. 醛肼的 C-H 三氟甲基硫代反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-12 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.242
Victor Levet, Balu Ramesh, Congyang Wang, Tatiana Besset
{"title":"C-H Trifluoromethylthiolation of aldehyde hydrazones.","authors":"Victor Levet, Balu Ramesh, Congyang Wang, Tatiana Besset","doi":"10.3762/bjoc.20.242","DOIUrl":"10.3762/bjoc.20.242","url":null,"abstract":"<p><p>The selective C-H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C-SCF<sub>3</sub> bond was achieved under oxidative and mild reaction conditions in the presence of the readily available AgSCF<sub>3</sub> salt via a one-pot sequential process (28 examples, up to 91% yield). Mechanistic investigations revealed that AgSCF<sub>3</sub> was the active species in the transformation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2883-2890"},"PeriodicalIF":2.2,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11571951/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667110","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions. 通过基于异氰酸酯的多组分反应合成吡咯融合二苯并氧氮杂卓/二苯并硫氮杂卓/三唑并二氮杂卓衍生物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-11 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.241
Marzieh Norouzi, Mohammad Taghi Nazeri, Ahmad Shaabani, Behrouz Notash
{"title":"Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions.","authors":"Marzieh Norouzi, Mohammad Taghi Nazeri, Ahmad Shaabani, Behrouz Notash","doi":"10.3762/bjoc.20.241","DOIUrl":"10.3762/bjoc.20.241","url":null,"abstract":"<p><p>An efficient and facile synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives was developed through the isocyanide-based multicomponent reaction of isocyanides, <i>gem</i>-diactivated olefins, and cyclic imines such as dibenzoxazepine, dibenzothiazepine, and triazolobenzodiazepine under solvent- and catalyst-free conditions. Purposefully, this approach produced various bioactive scaffolds using environmentally friendly, mild, and simple conditions. Due to their bioactive moieties, these compounds with exclusive fluorescence properties may attract great attention in biomedical applications, clinical diagnostics, and conjugate materials.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2870-2882"},"PeriodicalIF":2.2,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11571948/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity. 靛蓝、靛红和异靛蓝的 N-糖苷：蓝色、红色和黄色糖及其抗癌活性。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-08 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.240
Peter Langer
{"title":"<i>N</i>-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity.","authors":"Peter Langer","doi":"10.3762/bjoc.20.240","DOIUrl":"https://doi.org/10.3762/bjoc.20.240","url":null,"abstract":"<p><p>Indigo, indirubin, and isoindigo derivatives have been used for centuries as pigments. Since the 1990s, a new aspect of the chemistry of this type of compounds is their activity against various types of cancer. <i>N</i>-Glycosides of indigo, indirubin, and isoindigo, blue, red, and yellow sugars, turned out to be of special interest because of their high cancerostatic activity and structural novelty. The present article provides an account on the synthesis and anticancer activity of these compounds.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2840-2869"},"PeriodicalIF":2.2,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552416/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614056","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides. 使用由烷基溴化物生成的有机锌试剂多组分合成 α-支链胺。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-07 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.239
Baptiste Leroux, Alexis Beaufils, Federico Banchini, Olivier Jackowski, Alejandro Perez-Luna, Fabrice Chemla, Marc Presset, Erwan Le Gall
{"title":"Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides.","authors":"Baptiste Leroux, Alexis Beaufils, Federico Banchini, Olivier Jackowski, Alejandro Perez-Luna, Fabrice Chemla, Marc Presset, Erwan Le Gall","doi":"10.3762/bjoc.20.239","DOIUrl":"https://doi.org/10.3762/bjoc.20.239","url":null,"abstract":"<p><p>The use of alkylzinc bromides in the multicomponent Mannich reaction is described. Heteroleptic organozinc compounds were obtained in THF or 2-MeTHF by direct insertion of zinc dust into the C-Br bond of alkyl bromides. It was found that the presence of a stoichiometric amount of LiCl was essential for the efficiency of the subsequent three-component coupling with aldehydes and amines. A variety of primary, secondary, and tertiary organozinc reagents as well as secondary amines and aromatic aldehydes could be used for the straightforward preparation of α-branched amines. Interestingly, whereas previously reported work describing the preparation and reaction of organozinc iodides in acetonitrile showed higher reactivity of secondary organozinc reagents over primary ones, reactions in THF in the presence of LiCl led to opposite results, with higher reactivity of primary organozinc reagents.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2834-2839"},"PeriodicalIF":2.2,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552408/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614071","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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