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Divergent Synthesis of Trifluoromethyl Ketones via Photoredox Activation of Halotrifluoroacetones 通过光氧化活化卤代三氟丙酮分歧合成三氟甲基酮
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-09-25 DOI: 10.1002/hlca.202400125
Rahul Giri, Mathias Kissling, Egor Zhilin, Anthony J. Fernandes, Quentin E. L. Ordan, Dmitry Katayev
{"title":"Divergent Synthesis of Trifluoromethyl Ketones via Photoredox Activation of Halotrifluoroacetones","authors":"Rahul Giri,&nbsp;Mathias Kissling,&nbsp;Egor Zhilin,&nbsp;Anthony J. Fernandes,&nbsp;Quentin E. L. Ordan,&nbsp;Dmitry Katayev","doi":"10.1002/hlca.202400125","DOIUrl":"https://doi.org/10.1002/hlca.202400125","url":null,"abstract":"<p>Fluorine's high electronegativity, lipophilicity, and metabolic stability make it a valuable element for drug design and development. Consequently, significant synthetic efforts have focused on introducing fluorine and fluorinated motifs into organic molecules, with the synthesis of trifluoromethyl ketones (TFMKs) recently attracting considerable attention. Building on our ongoing research on radical organofluorine chemistry, we present herein the divergent synthesis of trifluoromethyl ketones directly from olefins using readily available chloro- and bromotrifluoroacetone as synthetic precursors of the trifluoroacetonyl radical under photoredox catalysis. Mechanistic studies revealed that the divergence is attained through radical polar crossover (RPC) and hydrogen atom transfer (HAT) mechanisms.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 10","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400125","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142540850","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
Cover Picture: (Helv. Chim. Acta 9/2024) 封面图片：（Helv.）
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-09-13 DOI: 10.1002/hlca.202470901
{"title":"Cover Picture: (Helv. Chim. Acta 9/2024)","authors":"","doi":"10.1002/hlca.202470901","DOIUrl":"https://doi.org/10.1002/hlca.202470901","url":null,"abstract":"<p>\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 9","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202470901","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142231085","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
Cover Picture: (Helv. Chim. Acta 8/2024) 封面图片：（Helv.）
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-08-19 DOI: 10.1002/hlca.202470801
{"title":"Cover Picture: (Helv. Chim. Acta 8/2024)","authors":"","doi":"10.1002/hlca.202470801","DOIUrl":"https://doi.org/10.1002/hlca.202470801","url":null,"abstract":"<p>\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 8","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202470801","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142002589","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
Micelle Enabled Buchwald-Hartwig Amination in Water with the Bening by Design Surfactant TPGS-750-M for the Synthesis of the JAK Inhibitor 4-((2-Chlorophenyl)amino)-6-((6-methylpyridin-2-yl)amino)nicotinamide 在水中利用 Micelle Enabled Buchwald-Hartwig Amination 与 Bening by Design 表面活性剂 TPGS-750-M 合成 JAK 抑制剂 4-((2-氯苯基)氨基)-6-((6-甲基吡啶-2-基)氨基)烟酰胺
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-08-11 DOI: 10.1002/hlca.202400094
Hao Jiang, Bin Wu, Dominik Rufle, Liping Wang, Min Shi, Michael Parmentier, Fabrice Gallou
{"title":"Micelle Enabled Buchwald-Hartwig Amination in Water with the Bening by Design Surfactant TPGS-750-M for the Synthesis of the JAK Inhibitor 4-((2-Chlorophenyl)amino)-6-((6-methylpyridin-2-yl)amino)nicotinamide","authors":"Hao Jiang,&nbsp;Bin Wu,&nbsp;Dominik Rufle,&nbsp;Liping Wang,&nbsp;Min Shi,&nbsp;Michael Parmentier,&nbsp;Fabrice Gallou","doi":"10.1002/hlca.202400094","DOIUrl":"10.1002/hlca.202400094","url":null,"abstract":"<p>An efficient and scalable Buchwald-Hartwig amination towards the synthesis of the API candidate 4-((2-Chlorophenyl)amino)-6-((6-methylpyridin-2-yl)amino)nicotinamide as a JAK inhibitor was described. The process was developed using water and a water-miscible co-solvent. It was facilitated by the benign by design surfactant TPGS-750-M, that promoted the robust and reliable preparation of our target compound in high yields, with improved reaction profile and via an operationally simple protocol.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 9","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141930096","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Telescopic, Scalable and Industrially Feasible Method for the Synthesis of Antidepressant Drug, Moclobemide 合成抗抑郁药物莫氯苯甲酰胺的可伸缩、可扩展和工业上可行的方法
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-07-16 DOI: 10.1002/hlca.202400075
Akanksha Keshri, Anjali Gupta, Upma Gulati, Tara Datt Bhatt, Maneesh Kashyap, Joydev K. Laha
{"title":"A Telescopic, Scalable and Industrially Feasible Method for the Synthesis of Antidepressant Drug, Moclobemide","authors":"Akanksha Keshri,&nbsp;Anjali Gupta,&nbsp;Upma Gulati,&nbsp;Tara Datt Bhatt,&nbsp;Maneesh Kashyap,&nbsp;Joydev K. Laha","doi":"10.1002/hlca.202400075","DOIUrl":"10.1002/hlca.202400075","url":null,"abstract":"<p>An improved, scalable, industrially feasible telescopic process for multigram synthesis of highly commercialized antidepressant drug, moclobemide has been developed. Unlike the conventional approaches, this process enjoys the privilege of being an economical, operationally simple, effectively scalable, and quantitative method for the synthesis of amide-containing drug moclobemide, showcasing easy isolation and purification without the aid of column chromatography. An environmentally benign reagent combination of TBN and NHS very effectively converts the acyl source, 4-chlorobenzaldehyde into its <i>N</i>-hydroxysuccinimide ester intermediate, which simply affords the drug molecule after nucleophilic substitution with the amine source. The synthetic process has successfully been scaled-up upto ~145 g scale with 75 % overall yield and &gt;95 % first crop HPLC purity.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 9","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141642620","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Conversion of Isoxazoles to Functionalized Pyrrole and Isoquinoline Derivatives via ROCC Mechanism 通过 ROCC 机制将异噁唑转化为功能化吡咯和异喹啉衍生物
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-07-15 DOI: 10.1002/hlca.202400057
Dr. Karri Raghavulu, Varukolu Shanker, Dr. Ramakrishna Gudipati, Prof. Dr. Keloth Basavaiah, Dr. Raju Doddipalla, Dr. Mahipal Yadav, Dr. Satyanarayana Yennam, Dr. Manoranjan Behera
{"title":"Conversion of Isoxazoles to Functionalized Pyrrole and Isoquinoline Derivatives via ROCC Mechanism","authors":"Dr. Karri Raghavulu,&nbsp;Varukolu Shanker,&nbsp;Dr. Ramakrishna Gudipati,&nbsp;Prof. Dr. Keloth Basavaiah,&nbsp;Dr. Raju Doddipalla,&nbsp;Dr. Mahipal Yadav,&nbsp;Dr. Satyanarayana Yennam,&nbsp;Dr. Manoranjan Behera","doi":"10.1002/hlca.202400057","DOIUrl":"10.1002/hlca.202400057","url":null,"abstract":"<p>Herein, we report a new method for the synthesis of functionalized pyrrole and isoquinoline derivatives using isoxazole based precursors. The reaction proceeds through the ring opening and ring closing cascade mechanism (ROCC) to afford pyrrole or isoquinoline derivatives in good to excellent yields under very mild experimental conditions. Product outcome relies on the strategic placement of different substituents on the isoxazole moiety. The present method is also applicable to synthesize functionalized isoquinolone derivatives.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 10","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141645339","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Cover Picture: (Helv. Chim. Acta 7/2024) 封面图片：（Helv.）
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-07-15 DOI: 10.1002/hlca.202470701
{"title":"Cover Picture: (Helv. Chim. Acta 7/2024)","authors":"","doi":"10.1002/hlca.202470701","DOIUrl":"https://doi.org/10.1002/hlca.202470701","url":null,"abstract":"<p> \u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 7","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202470701","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141624500","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
Potential of miRNA as Imaging Targets for PET miRNA 作为 PET 成像靶点的潜力
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-07-09 DOI: 10.1002/hlca.202400014
Simon H. Zientek, Stephen Thompson, Franklin I. Aigbirhio, Selena Milicevic Sephton
{"title":"Potential of miRNA as Imaging Targets for PET","authors":"Simon H. Zientek,&nbsp;Stephen Thompson,&nbsp;Franklin I. Aigbirhio,&nbsp;Selena Milicevic Sephton","doi":"10.1002/hlca.202400014","DOIUrl":"10.1002/hlca.202400014","url":null,"abstract":"<p>Positron Emission Tomography (PET) is an important part of the medical imaging field which is continually exploring novel biological targets as exemplified by PET imaging of neuroinflammation. Due to limitations stemming from either sub-optimal biological targets or a lack of available selective radiotracers, alternative biomarkers and PET imaging agent candidates are considered. One such possible target is microRNA (miRNA) and herein, we discuss the potential of miRNA for PET imaging. With the aim of addressing key strategies for imaging miRNA with PET, we identify three distinct approaches as follows: small molecules directly targeting miRNA, small molecules indirectly targeting Argonaute 2 (AGO2)-protein complexes, and direct chemical modification of antisense oligonucleotides. The radiosynthetic approaches are based on the methods of direct radiolabelling of respective antisense oligonucleotides and several examples are described herein, showcasing the potential of miRNA in PET imaging. Whilst these approaches offer different radiolabelling strategies, application of these radiolabelled molecules towards PET imaging of miRNA are scarce with only one, limited example applied to bone remodeling reported in the literature.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 8","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400014","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141577339","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
Platinum-Catalyzed Isomerization of Cyclopropenes to 1,3-Dienes 铂催化环丙烯与 1,3-二烯的异构化反应
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-07-05 DOI: 10.1002/hlca.202400105
Vladyslav Smyrnov, Antonin Homassel, Leander Choudhury, Jerome Waser
{"title":"Platinum-Catalyzed Isomerization of Cyclopropenes to 1,3-Dienes","authors":"Vladyslav Smyrnov,&nbsp;Antonin Homassel,&nbsp;Leander Choudhury,&nbsp;Jerome Waser","doi":"10.1002/hlca.202400105","DOIUrl":"10.1002/hlca.202400105","url":null,"abstract":"<p>Herein we report a platinum-catalyzed isomerization of cyclopropenes to 1,3-dienes. Diverse dienylated alcohols were obtained in 42–98 % yield. The synthetic potential of the products was demonstrated by their use in Diels–Alder cycloadditions with various dienophiles. Isotope labelling studies provide strong support for a mechanism involving pericyclic [1,5]-σ-bond rearrangement of a vinyl platinum carbene intermediate.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 9","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400105","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141577340","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
Fluorinated-Thiolate Osmium(III) and Osmium(IV) Complexes Bearing N,N-diethyldithiocarbamate and Substituted Phosphines. Synthesis, Crystal Structures and DFT-Studies 含 N,N-二乙基二硫代氨基甲酸酯和取代膦的氟硫酸盐锇(III)和锇(IV)配合物：合成、晶体结构和 DFT 研究
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-07-05 DOI: 10.1002/hlca.202400066
Bertín Anzaldo, Andrés Álvarez-García, Sylvain Bernès, Armando Ramírez-Monroy, Maribel Arroyo-Carranza
{"title":"Fluorinated-Thiolate Osmium(III) and Osmium(IV) Complexes Bearing N,N-diethyldithiocarbamate and Substituted Phosphines. Synthesis, Crystal Structures and DFT-Studies","authors":"Bertín Anzaldo,&nbsp;Andrés Álvarez-García,&nbsp;Sylvain Bernès,&nbsp;Armando Ramírez-Monroy,&nbsp;Maribel Arroyo-Carranza","doi":"10.1002/hlca.202400066","DOIUrl":"10.1002/hlca.202400066","url":null,"abstract":"<p>The paramagnetic osmium(III) [Os(SR<sub>F</sub>)(S<sub>2</sub>CNEt<sub>2</sub>)<sub>2</sub>(P(C<sub>6</sub>H<sub>4</sub>X-4)<sub>3</sub>)] (R<sub>F</sub>=C<sub>6</sub>F<sub>4</sub>H−4, C<sub>6</sub>F<sub>5</sub>; X=OCH<sub>3</sub>, CH<sub>3</sub>, F) (<b>1–6</b>) along with diamagnetic osmium(IV) [Os(SR<sub>F</sub>)<sub>2</sub>(S<sub>2</sub>CNEt<sub>2</sub>)<sub>2</sub>] (<b>7–8</b>) complexes were obtained from [Os(SR<sub>F</sub>)<sub>4</sub>(P(C<sub>6</sub>H<sub>4</sub>-X)<sub>3</sub>)] and NaS<sub>2</sub>CNEt<sub>2</sub>, which were characterized by FAB mass spectrometry, IR spectroscopy, single crystal X-ray diffraction, and for the diamagnetic <b>7</b> also by NMR. TD-DFT calculations were performed to simulate the absorption spectra of complexes. In the visible region, LMCT transitions contribute to the calculated intensities, which are somewhat related to the color of the synthesized compounds. In the ultraviolet region, the phosphine ligand plays a significant role in MLCT transitions, which results in Os(III) complexes exhibiting an intense band in that region. Topological analysis and electron localization function (ELF) maps calculated for <b>6</b> and <b>7</b> confirm the strong ionic character of the Os−S coordination bonds formed by the thiophenolate and dithiocarbamate ligands. This comprehensive study provides information on the structure, bonding, and electronic properties of osmium complexes, for potential applications in catalysis, materials science, and biological systems.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 9","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141577341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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