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Literature DB >> 27917423

Metal-free ¹⁸F-labeling of aryl-CF₂H via nucleophilic radiofluorination and oxidative C-H activation.

Gengyang Yuan¹, Feng Wang², Nickeisha A Stephenson³, Lu Wang³, Benjamin H Rotstein³, Neil Vasdev³, Pingping Tang², Steven H Liang³.

Abstract

A metal-free and selective method to form [18F]aryl-CF2H through nucleophilic radiofluorination of benzyl (pseudo)halides and oxidative C-H activation of benzylic C-H bonds has been developed. The method is operationally simple and tolerates a variety of electron-neutral/deficient arenes and heteroarenes.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2016 PMID： 27917423 PMCID： PMC5179041 DOI： 10.1039/c6cc07913j

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

23 in total

1. Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate).

Authors: Harriet Teare; Edward G Robins; Anna Kirjavainen; Sarita Forsback; Graham Sandford; Olof Solin; Sajinder K Luthra; Véronique Gouverneur
Journal: Angew Chem Int Ed Engl Date: 2010-09-10 Impact factor: 15.336

Review 2. Selectfluor: mechanistic insight and applications.

Authors: Paul T Nyffeler; Sergio Gonzalez Durón; Michael D Burkart; Stéphane P Vincent; Chi-Huey Wong
Journal: Angew Chem Int Ed Engl Date: 2004-12-27 Impact factor: 15.336

3. Transition-metal-free C-H oxidative activation: persulfate-promoted selective benzylic mono- and difluorination.

Authors: Jing-jing Ma; Wen-bin Yi; Guo-ping Lu; Chun Cai
Journal: Org Biomol Chem Date: 2015-03-14 Impact factor: 3.876

4. Late-stage [¹⁸F]Fluorination: New Solutions to Old Problems.

Authors: Allen F Brooks; Joseph J Topczewski; Naoko Ichiishi; Melanie S Sanford; Peter J H Scott
Journal: Chem Sci Date: 2014-12-01 Impact factor: 9.825

5. Nanomolar potency and metabolically stable inhibitors of kidney urea transporter UT-B.

Authors: Marc O Anderson; Jicheng Zhang; Yan Liu; Chenjuan Yao; Puay-Wah Phuan; A S Verkman
Journal: J Med Chem Date: 2012-06-19 Impact factor: 7.446

Review 6. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors: Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal: Chem Rev Date: 2013-12-03 Impact factor: 60.622

7. 1,1-Difluoroethyl-substituted triazolothienopyrimidines as inhibitors of a human urea transport protein (UT-B): new analogs and binding model.

Authors: Y Liu; C Esteva-Font; C Yao; P W Phuan; A S Verkman; M O Anderson
Journal: Bioorg Med Chem Lett Date: 2013-04-01 Impact factor: 2.823

8. Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.

Authors: Satoshi Mizuta; Ida S R Stenhagen; Miriam O'Duill; Jamie Wolstenhulme; Anna K Kirjavainen; Sarita J Forsback; Matthew Tredwell; Graham Sandford; Peter R Moore; Mickael Huiban; Sajinder K Luthra; Jan Passchier; Olof Solin; Véronique Gouverneur
Journal: Org Lett Date: 2013-05-20 Impact factor: 6.005

Metal-free ¹⁸F-labeling of aryl-CF₂H via nucleophilic radiofluorination and oxidative C-H activation.

1. Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate).

Review 2. Selectfluor: mechanistic insight and applications.

3. Transition-metal-free C-H oxidative activation: persulfate-promoted selective benzylic mono- and difluorination.

4. Late-stage [¹⁸F]Fluorination: New Solutions to Old Problems.

5. Nanomolar potency and metabolically stable inhibitors of kidney urea transporter UT-B.

Review 6. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

7. 1,1-Difluoroethyl-substituted triazolothienopyrimidines as inhibitors of a human urea transport protein (UT-B): new analogs and binding model.

8. Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.

9. Direct Difluoromethylation of Aryl Halides via Base Metal Catalysis at Room Temperature.

10. Copper-catalyzed [18F]fluorination of (mesityl)(aryl)iodonium salts.

Review 1. Closing the gap between ¹⁹F and ¹⁸F chemistry.

Review 2. Selectfluor: mechanistic insight and applications.

Review 6. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Review 1. Closing the gap between 19F and 18F chemistry.

Review 1. Closing the gap between ¹⁹F and ¹⁸F chemistry.