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Dr. Matthew Tredwell Dr. Sean M. Preshlock Nicholas J. Taylor Dr. Stefan Gruber Dr. Mickael Huiban Dr. Jan Passchier Dr. Joël Mercier Dr. Christophe Génicot Prof. Véronique Gouverneur 《Angewandte Chemie (International ed. in English)》2014,53(30):7751-7755
Molecules labeled with fluorine‐18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (SNAr) with [18F]F?. In the ideal case, the 18F fluorination of these substrates would be performed through reaction of [18F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of 18F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [18F]KF/K222 and [Cu(OTf)2(py)4] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[18F]fluoro‐L ‐DOPA, 6‐[18F]fluoro‐m‐tyrosine, and the translocator protein (TSPO) PET ligand [18F]DAA1106. 相似文献
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Inside Cover: A General Copper‐Mediated Nucleophilic 18F Fluorination of Arenes (Angew. Chem. Int. Ed. 30/2014) 下载免费PDF全文
Dr. Matthew Tredwell Dr. Sean M. Preshlock Nicholas J. Taylor Dr. Stefan Gruber Dr. Mickael Huiban Dr. Jan Passchier Dr. Joël Mercier Dr. Christophe Génicot Prof. Véronique Gouverneur 《Angewandte Chemie (International ed. in English)》2014,53(30):7678-7678
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A Localized Tolerance in the Substrate Specificity of the Fluorinase Enzyme enables “Last‐Step” 18F Fluorination of a RGD Peptide under Ambient Aqueous Conditions 下载免费PDF全文
Stephen Thompson Qingzhi Zhang Mayca Onega Stephen McMahon Ian Fleming Sharon Ashworth James H. Naismith Jan Passchier David O'Hagan 《Angewandte Chemie (International ed. in English)》2014,53(34):8913-8918
A strategy for last‐step 18F fluorination of bioconjugated peptides is reported that exploits an “Achilles heel” in the substrate specificity of the fluorinase enzyme. An acetylene functionality at the C‐2 position of the adenosine substrate projects from the active site into the solvent. The fluorinase catalyzes a transhalogenation of 5′‐chlorodeoxy‐2‐ethynyladenosine (ClDEA) to 5′‐fluorodeoxy‐2‐ethynyladenosine (FDEA). Extending a polyethylene glycol linker from the terminus of the acetylene allows the presentation of bioconjugation cargo to the enzyme for 18F labelling. The method uses an aqueous solution (H218O) of [18F]fluoride generated by the cyclotron and has the capacity to isotopically label peptides of choice for positron emission tomography (PET). 相似文献
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Stefanie K. Fehler Dr. Simone Maschauer Dr. Sarah B. Höfling Amelie L. Bartuschat Dr. Nuska Tschammer Dr. Harald Hübner Prof. Dr. Peter Gmeiner Prof. Dr. Olaf Prante Prof. Dr. Markus R. Heinrich 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(2):370-375
Introduction of [18F]fluoride ion into the aromatic core of phenylazocarboxylic esters was achieved in only 30 seconds, with radiochemical yields of up to 95 % (85(±10) %). For labeling purposes, the resulting 18F‐substituted azoester can be further converted in radical‐arylation reactions to give biaryls, or in substitutions at its carbonyl unit to produce azocarboxamides. 相似文献
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Dr. Matthew Tredwell Prof. Véronique Gouverneur 《Angewandte Chemie (International ed. in English)》2012,51(46):11426-11437
Molecular imaging has witnessed an upsurge in growth, with positron emission tomography leading the way. This trend has encouraged numerous synthetic chemists to enter the field of 18F‐radiochemistry and provide generic solutions to address the well‐recognized challenges of late‐stage fluorination. This Minireview focuses on recent developments in the 18F‐labeling of aromatic substrates. 相似文献
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Aileen Höhne Lian Yu Linjing Mu Dr. Markus Reiher Prof. Dr. Ulrike Voigtmann Dr. Ulrich Klar Dr. Keith Graham Dr. P. August Schubiger Prof. Dr. Simon M. Ametamey Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(15):3736-3743
Water stable! Radiochemists have recently discovered silicon chemistry as a tool for the introduction of 18F into biomolecules for positron emission tomography (PET) imaging. 18F‐labeled PET tracers must be stable towards defluorination under physiological conditions. Here, a theoretical model of organofluorosilane hydrolysis is developed that correlates with the experimentally determined hydrolytic half‐lives and allows estimation of the stability of newly designed compounds (see scheme).
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Dr. Bjarke S. Donslund Nicolaj Inunnguaq Jessen Giulio Bertuzzi Dr. Maxime Giardinetti Dr. Teresa A. Palazzo Mette Louise Christensen Prof. Dr. Karl Anker Jørgensen 《Angewandte Chemie (International ed. in English)》2018,57(40):13182-13186
The first peri‐ and stereoselective [10+4] cycloaddition between catalytically generated amino isobenzofulvenes and electron‐deficient dienes is described. The highly stereoselective catalytic [10+4] cycloaddition exhibits a broad scope with high yields, reflecting a robust higher‐order cycloaddition. Experimental and computational investigations support a kinetic distribution of intermediate rotamers dictating the enantioselectivity, which relies heavily on additive effects. 相似文献
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Hang Shi Augustin Braun Lu Wang Prof. Dr. Steven H. Liang Prof. Dr. Neil Vasdev Prof. Dr. Tobias Ritter 《Angewandte Chemie (International ed. in English)》2016,55(36):10786-10790
A general method for the synthesis of [18F]difluoromethylarenes from [18F]fluoride for radiopharmaceutical discovery is reported. The method is practical, operationally simple, tolerates a wide scope of functional groups, and enables the labeling of a variety of arenes and heteroarenes with radiochemical yields (RCYs, not decay‐corrected) from 10 to 60 %. The 18F‐fluorination precursors are readily prepared from aryl chlorides, bromides, iodides, and triflates. Seven 18F‐difluoromethylarene drug analogues and radiopharmaceuticals including Claritin, fluoxetine (Prozac), and [18F]DAA1106 were synthesized to show the potential of the method for applications in PET radiopharmaceutical design. 相似文献
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N‐Heterocyclic Carbene Catalyzed Enantioselective α‐Fluorination of Aliphatic Aldehydes and α‐Chloro Aldehydes: Synthesis of α‐Fluoro Esters,Amides, and Thioesters 下载免费PDF全文
Dr. Xiuqin Dong Dr. Wen Yang Dr. Weimin Hu Prof. Dr. Jianwei Sun 《Angewandte Chemie (International ed. in English)》2015,54(2):660-663
The asymmetric fluorination of azolium enolates that are generated from readily available simple aliphatic aldehydes or α‐chloro aldehydes and N‐heterocyclic carbenes (NHCs) is described. The process significantly expands the synthetic utility of NHC‐catalyzed fluorination and provides facile access to a wide range of α‐fluoro esters, amides, and thioesters with excellent enantioselectivity. Pyrazole was identified as an excellent acyl transfer reagent for catalytic amide formation. 相似文献
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A Direct,Concise, and Enantioselective Synthesis of 2‐Substituted 4,4,4‐Trifluorobutane‐1,3‐diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde 下载免费PDF全文
Prof. Dr. Kazumasa Funabiki Yudai Furuno Yosuke Yano Yuta Sakaida Dr. Yasuhiro Kubota Prof. Dr. Masaki Matsui 《化学:亚洲杂志》2015,10(12):2701-2707
A direct, concise, and enantioselective synthesis of 2‐substituted 4,4,4‐trifluorobutane‐1,3‐diols based on the organocatalytic asymmetric direct aldol reaction of an ethyl hemiacetal of trifluoroacetaldehyde with various aldehydes was examined. A catalytic amount (30 mol %) of commercially available and inexpensive l ‐prolinamide is quite effective as an organocatalyst for the catalytic in situ generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal, and a successive asymmetric direct aldol reaction with various aldehydes in dichloromethane at 0 °C, followed by reduction with sodium borohydride, gives 2‐substituted 4,4,4‐trifluorobutane‐1,3‐diols in moderate to good yields (31–84 %) with low diastereoselectivities and good to excellent enantioselectivities (64–97 % ee). 相似文献
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From 2000, our two research groups independently and simultaneously designed and developed a novel family of electrophilic fluorinating reagents based on the use of Cinchona alkaloids. The chiral N-fluoro ammonium salts demonstrated the highest efficiency compared to prior art in enantioselective electrophilic fluorination for a wide range of substrates. In this account, we tell our respective stories, how the same idea germinated in our laboratories, the characterization of the chiral reagents, the use in stoichiometric quantity then the development of a catalytic version, the application to the synthesis of chiral fluorinated molecules of pharmaceutical interest, and finally the exploitation of our reagents by other teams and for other applications. 相似文献
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Miller PW Long NJ Vilar R Gee AD 《Angewandte Chemie (International ed. in English)》2008,47(47):8998-9033
Positron emission tomography (PET) is a powerful and rapidly developing area of molecular imaging that is used to study and visualize human physiology by the detection of positron-emitting radiopharmaceuticals. Information about metabolism, receptor/enzyme function, and biochemical mechanisms in living tissue can be obtained directly from PET experiments. Unlike magnetic resonance imaging (MRI) or computerized tomography (CT), which mainly provide detailed anatomical images, PET can measure chemical changes that occur before macroscopic anatomical signs of a disease are observed. PET is emerging as a revolutionary method for measuring body function and tailoring disease treatment in living subjects. The development of synthetic strategies for the synthesis of new positron-emitting molecules is, however, not trivial. This Review highlights key aspects of the synthesis of PET radiotracers with the short-lived positron-emitting radionuclides (11)C, (18)F, (15)O, and (13)N, with emphasis on the most recent strategies. 相似文献
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Ljuba Iovkova Dipl. Chem. Björn Wängler Dr. Esther Schirrmacher Dr. Ralf Schirrmacher Prof. Dr. Gabriele Quandt Dipl. Chem. Guido Boening Dr. Markus Schürmann Klaus Jurkschat Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(9):2140-2147
Broad spectrum : Novel para‐functionalized aryl‐di‐tert‐butylfluorosilanes, p‐(tBu2FSi)C6H4X (X=functional group), have been made available and broaden the spectrum of silicon‐based 18F acceptors (SiFAs) for potential PET applications. For example, the [18F]maleimido derivative 1 has been employed for the synthesis of [18F] 1 ‐ labeled rat serum albumin (RSA), the applicability of which for PET has been verified by in vivo experiments.