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Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures. 三氮杂三联硒阳离子的离子配对组装依赖于阴离子，会干扰堆叠结构。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-10 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.215
Yohei Haketa, Takuma Matsuda, Hiromitsu Maeda
{"title":"Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures.","authors":"Yohei Haketa, Takuma Matsuda, Hiromitsu Maeda","doi":"10.3762/bjoc.20.215","DOIUrl":"https://doi.org/10.3762/bjoc.20.215","url":null,"abstract":"<p><p>Ion pairs of <i>N</i>-(2,6-dimethylphenyl)-substituted triazatriangulenium (TATA<sup>+</sup>) cation with various counteranions were synthesized to investigate the interactions for the bulky cation. Single-crystal X-ray analysis of the TATA<sup>+</sup> ion pairs revealed solid-state ion-pairing assemblies without stacking at the cationic π-planes. The TATA<sup>+</sup> cation showed counteranion-dependent assembly structures, with smaller counteranions located at the top of TATA<sup>+</sup> and bulkier counteranions displaced from the TATA<sup>+</sup> plane to interact with the surrounding TATA<sup>+</sup>.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2567-2576"},"PeriodicalIF":2.2,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11472656/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142456979","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
A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis. 通过阳极氧化、阴极还原和配对电解分类，回顾电化学和光电化学后期功能化的最新进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-09 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.214
Nian Li, Ruzal Sitdikov, Ajit Prabhakar Kale, Joost Steverlynck, Bo Li, Magnus Rueping
{"title":"A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis.","authors":"Nian Li, Ruzal Sitdikov, Ajit Prabhakar Kale, Joost Steverlynck, Bo Li, Magnus Rueping","doi":"10.3762/bjoc.20.214","DOIUrl":"https://doi.org/10.3762/bjoc.20.214","url":null,"abstract":"<p><p>With the resurgence of electrosynthesis in organic chemistry, there is a significant increase in the number of routes available for late-stage functionalization (LSF) of drugs. Electrosynthetic methods, which obviate the need for hazardous chemical oxidants or reductants, offer unprecedented control of reactions through the continuous variation of the applied potential and the possibility of combination with photochemical processes. This capability is a substantial advantage for performing electrochemical or photoelectrochemical LSF. Ultimately, these protocols are poised to become a vital component of the medicinal chemist's toolkit. In this review, we discuss electrochemical protocols that have been demonstrated to be applicable for the LSF of pharmaceutical drugs, their derivatives, and natural substrates. We present and analyze representative examples to illustrate the potential of electrochemistry or photoelectrochemistry for the LSF of valuable molecular scaffolds.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2500-2566"},"PeriodicalIF":2.2,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11472660/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142456978","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
Visible-light-mediated flow protocol for Achmatowicz rearrangement. 以可见光为媒介的 Achmatowicz 重排流动方案。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-08 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.213
Joachyutharayalu Oja, Sanjeev Kumar, Srihari Pabbaraja
{"title":"Visible-light-mediated flow protocol for Achmatowicz rearrangement.","authors":"Joachyutharayalu Oja, Sanjeev Kumar, Srihari Pabbaraja","doi":"10.3762/bjoc.20.213","DOIUrl":"https://doi.org/10.3762/bjoc.20.213","url":null,"abstract":"<p><p>The batch processes of APIs/pharmaceutical synthesis are prone to suffer significant limitations, including longer process time, shortage of skilled manpower, laborious post-synthetic work-up, etc. To address the inherent limitations of batch processes, a novel approach was undertaken, resulting in the establishment and development of a visible light-assisted modular photo-flow reactor with a seamlessly integrated post-synthetic work-up procedure enabling the efficient synthesis of dihydropyranones from furfuryl alcohols. The reaction uses sun light as green energy source, and the novel photo-flow reactor platform developed with an integrated system enabling a downstream process in a time and labor-efficient manner which facilitates the Achmatowicz rearrangement, resulting in a fast (10 min) formation of the dihydropyranone products.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2493-2499"},"PeriodicalIF":2.2,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11472655/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142456981","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
Machine learning-guided strategies for reaction conditions design and optimization. 以机器学习为指导的反应条件设计和优化策略。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-04 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.212
Lung-Yi Chen, Yi-Pei Li
{"title":"Machine learning-guided strategies for reaction conditions design and optimization.","authors":"Lung-Yi Chen, Yi-Pei Li","doi":"10.3762/bjoc.20.212","DOIUrl":"https://doi.org/10.3762/bjoc.20.212","url":null,"abstract":"<p><p>This review surveys the recent advances and challenges in predicting and optimizing reaction conditions using machine learning techniques. The paper emphasizes the importance of acquiring and processing large and diverse datasets of chemical reactions, and the use of both global and local models to guide the design of synthetic processes. Global models exploit the information from comprehensive databases to suggest general reaction conditions for new reactions, while local models fine-tune the specific parameters for a given reaction family to improve yield and selectivity. The paper also identifies the current limitations and opportunities in this field, such as the data quality and availability, and the integration of high-throughput experimentation. The paper demonstrates how the combination of chemical engineering, data science, and ML algorithms can enhance the efficiency and effectiveness of reaction conditions design, and enable novel discoveries in synthetic chemistry.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2476-2492"},"PeriodicalIF":2.2,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457048/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387569","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
HFIP as a versatile solvent in resorcin[n]arene synthesis. HFIP 作为合成间苯二酚[n]炔的多功能溶剂。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-02 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.211
Hormoz Khosravi, Valeria Stevens, Raúl Hernández Sánchez
{"title":"HFIP as a versatile solvent in resorcin[<i>n</i>]arene synthesis.","authors":"Hormoz Khosravi, Valeria Stevens, Raúl Hernández Sánchez","doi":"10.3762/bjoc.20.211","DOIUrl":"https://doi.org/10.3762/bjoc.20.211","url":null,"abstract":"<p><p>Herein, we present 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as an efficient solvent for synthesizing resorcin[<i>n</i>]arenes in the presence of catalytic amounts of HCl at ambient temperature and within minutes. Remarkably, resorcinols with electron-withdrawing groups and halogens, which are reported in the literature as the most challenging precursors in this cyclization, are tolerated. This method leads to a variety of 2-substituted resorcin[<i>n</i>]arenes in a single synthetic step with isolated yields up to 98%.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2469-2475"},"PeriodicalIF":2.2,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457071/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387567","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
Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams. 光氧化催化烯与β-内酰胺的分子内亲核酰胺化反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-01 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.210
Valentina Giraldi, Giandomenico Magagnano, Daria Giacomini, Pier Giorgio Cozzi, Andrea Gualandi
{"title":"Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams.","authors":"Valentina Giraldi, Giandomenico Magagnano, Daria Giacomini, Pier Giorgio Cozzi, Andrea Gualandi","doi":"10.3762/bjoc.20.210","DOIUrl":"https://doi.org/10.3762/bjoc.20.210","url":null,"abstract":"<p><p>The direct nucleophilic addition of amides to unfunctionalized alkenes via photoredox catalysis represents a facile approach towards functionalized alkylamides. Unfortunately, the scarce nucleophilicity of amides and competitive side reactions limit the utility of this approach. Herein, we report an intramolecular photoredox cyclization of alkenes with β-lactams in the presence of an acridinium photocatalyst. The approach uses an intramolecular nucleophilic addition of the β-lactam nitrogen atom to the radical cation photogenerated in the linked alkene moiety, followed by hydrogen transfer from the hydrogen atom transfer (HAT) catalyst. This process was used to successfully prepare 2-alkylated clavam derivatives.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2461-2468"},"PeriodicalIF":2.2,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457124/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387570","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
Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols. 高价碘介导的双烯丙基酰胺环化生成脯氨醇。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-30 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.209
Smaher E Butt, Konrad Kepski, Jean-Marc Sotiropoulos, Wesley J Moran
{"title":"Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols.","authors":"Smaher E Butt, Konrad Kepski, Jean-Marc Sotiropoulos, Wesley J Moran","doi":"10.3762/bjoc.20.209","DOIUrl":"https://doi.org/10.3762/bjoc.20.209","url":null,"abstract":"<p><p>A change in mechanism was observed in the hypervalent iodine-mediated cyclization of <i>N</i>-alkenylamides when the carbon chain between the alkene and the amide increased from two to three atoms. In the latter case, cyclization at the amide nitrogen to form the pyrrolidine ring was favored over cyclization at the amide oxygen. A DFT study was undertaken to rationalize the change in mechanism of this cyclization process. In addition, reaction conditions were developed, and the scope of this cyclization studied.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2455-2460"},"PeriodicalIF":2.2,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457059/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387568","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 and conformational analysis of pyran inter-halide analogues of ᴅ-talose. ᴅ-塔罗糖吡喃间卤化物类似物的合成和构象分析。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-27 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.208
Olivier Lessard, Mathilde Grosset-Magagne, Paul A Johnson, Denis Giguère
{"title":"Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose.","authors":"Olivier Lessard, Mathilde Grosset-Magagne, Paul A Johnson, Denis Giguère","doi":"10.3762/bjoc.20.208","DOIUrl":"10.3762/bjoc.20.208","url":null,"abstract":"<p><p>In this work, we describe the synthesis of halogenated pyran analogues of ᴅ-talose using a halo-divergent strategy from known 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-ᴅ-mannopyranose. In solution and in the solid-state, all analogues adopt standard <sup>4</sup> <i>C</i> <sub>1</sub>-like conformations despite 1,3-diaxial repulsion between the F2 and the C4 halogen. Moreover, the solid-state conformational analysis of halogenated pyrans reveals deviation in the intra-annular torsion angles arising from repulsion between the axial fluorine at C2 and the axial halogen at C4, which increases with the size of the halogen at C4 (F < Cl < Br < I). Crystal packing arrangements of pyran inter-halides show hydrogen bond acceptor and nonbonding interactions for the halogen at C4. Finally, density functional theory (DFT) calculations corroborate the preference of talose analogues to adopt a <sup>4</sup> <i>C</i> <sub>1</sub>-like conformation and a natural bonding orbital (NBO) analysis demonstrates the effects of hyperconjugation from C-F antibonding orbitals.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2442-2454"},"PeriodicalIF":2.2,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11443651/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360895","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
Phenylseleno trifluoromethoxylation of alkenes. 烯烃的苯基硒三氟甲氧基化。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-26 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.207
Clément Delobel, Armen Panossian, Gilles Hanquet, Frédéric R Leroux, Fabien Toulgoat, Thierry Billard
{"title":"Phenylseleno trifluoromethoxylation of alkenes.","authors":"Clément Delobel, Armen Panossian, Gilles Hanquet, Frédéric R Leroux, Fabien Toulgoat, Thierry Billard","doi":"10.3762/bjoc.20.207","DOIUrl":"10.3762/bjoc.20.207","url":null,"abstract":"<p><p>Trifluoromethoxylated molecules and selenylated compounds find a wide range of interesting applications, but separately. In order to combine the potential of these two motifs and to propose a new class of compounds, we have developed an electrophilic phenylseleno trifluoromethoxylation of alkenes, which leads to β-selenylated trifluoromethoxylated compounds or, upon subsequent reduction, to the trifluoromethoxylated ones.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2434-2441"},"PeriodicalIF":2.2,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11443662/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360894","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
Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles. 简便制备含氟 2,3-环氧丙酸酯及其与各种亲核物的环氧开环反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-25 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.206
Yutaro Miyashita, Sae Someya, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Takashi Yamazaki
{"title":"Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles.","authors":"Yutaro Miyashita, Sae Someya, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Takashi Yamazaki","doi":"10.3762/bjoc.20.206","DOIUrl":"10.3762/bjoc.20.206","url":null,"abstract":"<p><p>We describe herein a facile method to access 2,3-epoxyesters with fluorine-containing substituents at their 3-position starting from the corresponding enoates by utilization of the low-costed and easy-to-handle reagent, NaOCl·5H<sub>2</sub>O. Because very little has been disclosed about the reactivity of such 2,3-epoxyesters, their epoxy ring opening by a variety of nucleophiles was carried out and we succeeded in clarifying these chemo- as well as regioselective processes proceeding via the S<sub>N</sub>2 mechanism to mainly afford 2-substituted 3-hydroxyesters usually in a highly <i>anti</i> selective manner.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2421-2433"},"PeriodicalIF":2.2,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11443650/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360893","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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