Literature DB >> 29276938

(Radio)fluoroclick Reaction Enabled by a Hydrogen-Bonding Cluster.

Xiaojun Zeng1, Junling Li2, Chin K Ng2, Gerald B Hammond3, Bo Xu1.   

Abstract

We have developed a widely applicable nucleophilic (radio)fluoroclick reaction of ynamides with readily available and easy-to-handle KF(18 F). The reactions exhibited high functional-group tolerance and needed only an ambient atmosphere. This 18 F addition to C-C unsaturated bonds proceeded with extraordinarily high radiochemical yields.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkali fluorides; fluorination; hydrogen bonds; radiofluorination; ynamides

Year:  2018        PMID： 29276938      PMCID： PMC6233894          DOI： 10.1002/anie.201711341

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  48 in total

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2.  Synthesis, improved antisense activity and structural rationale for the divergent RNA affinities of 3'-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides.

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Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

3.  Chemo- and stereoselective synthesis of fluorinated enamides from ynamides in HF/pyridine: second-generation approach to potent ureas bioisosteres.

Authors:  Benoît Métayer; Guillaume Compain; Kévin Jouvin; Agnès Martin-Mingot; Christian Bachmann; Jérôme Marrot; Gwilherm Evano; Sébastien Thibaudeau
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4.  Late-stage [18F]Fluorination: New Solutions to Old Problems.

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Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

Review 5.  Fluorine-18 labelled building blocks for PET tracer synthesis.

Authors:  Dion van der Born; Anna Pees; Alex J Poot; Romano V A Orru; Albert D Windhorst; Danielle J Vugts
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6.  Cu-Catalyzed Click Reaction in Carbohydrate Chemistry.

Authors:  Vinod K Tiwari; Bhuwan B Mishra; Kunj B Mishra; Nidhi Mishra; Anoop S Singh; Xi Chen
Journal:  Chem Rev       Date:  2016-01-22       Impact factor: 60.622

7.  Hydrogen-bond promoted nucleophilic fluorination: concept, mechanism and applications in positron emission tomography.

Authors:  Ji-Woong Lee; Maria Teresa Oliveira; Hyeong Bin Jang; Sungyul Lee; Dae Yoon Chi; Dong Wook Kim; Choong Eui Song
Journal:  Chem Soc Rev       Date:  2016-08-22       Impact factor: 54.564

8.  Hydrogen Bonding to Hexafluoroisopropanol Controls the Oxidative Strength of Hypervalent Iodine Reagents.

Authors:  Ignacio Colomer; Christopher Batchelor-McAuley; Barbara Odell; Timothy J Donohoe; Richard G Compton
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9.  Coordination diversity in hydrogen-bonded homoleptic fluoride-alcohol complexes modulates reactivity.

Authors:  Keary M Engle; Lukas Pfeifer; George W Pidgeon; Guy T Giuffredi; Amber L Thompson; Robert S Paton; John M Brown; Véronique Gouverneur
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10.  Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids.

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Journal:  Org Lett       Date:  2015-11-14       Impact factor: 6.005
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  10 in total

1.  Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2.

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Journal:  Chem       Date:  2020-04-09       Impact factor: 22.804

2.  Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.

Authors:  Max Moskowitz; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336

Review 3.  Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

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Journal:  Front Chem       Date:  2022-06-29       Impact factor: 5.545

4.  Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol.

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Journal:  Chem Sci       Date:  2018-09-13       Impact factor: 9.825

Review 5.  Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

Authors:  Marek Grzybowski; Bartłomiej Sadowski; Holger Butenschön; Daniel T Gryko
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-03       Impact factor: 15.336

6.  Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes.

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7.  Hydrogen Bonding Phase-Transfer Catalysis with Alkali Metal Fluorides and Beyond.

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8.  Regio- and stereoselective thiocyanatothiolation of alkynes and alkenes by using NH4SCN and N-thiosuccinimides.

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Journal:  RSC Adv       Date:  2020-09-10       Impact factor: 4.036

9.  Cove-Edged Hexa-peri-hexabenzo-bis-peri-octacene: Molecular Conformations and Amplified Spontaneous Emission.

Authors:  Yanwei Gu; Victor Vega-Mayoral; Saül Garcia-Orrit; Dieter Schollmeyer; Akimitsu Narita; Juan Cabanillas-González; Zijie Qiu; Klaus Müllen
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10.  A Nanographene-Based Two-Dimensional Covalent Organic Framework as a Stable and Efficient Photocatalyst.

Authors:  Enquan Jin; Shuai Fu; Hiroki Hanayama; Matthew A Addicoat; Wenxin Wei; Qiang Chen; Robert Graf; Katharina Landfester; Mischa Bonn; Kai A I Zhang; Hai I Wang; Klaus Müllen; Akimitsu Narita
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-16       Impact factor: 16.823
  10 in total

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