Literature DB >> 33000949

Direct Radiofluorination of Arene C-H Bonds via Photoredox Catalysis Using a Peroxide as the Terminal Oxidant.

Li Wang1, Alexander R White2, Wei Chen1, Zhanhong Wu1, David A Nicewicz2, Zibo Li1.   

Abstract

Herein, we describe an organic photoredox system for direct arene C-H radiofluorination, using a peroxide oxidizing agent and LEDs as the light source. In conjunction with an optimized photocatalyst and a microtubing reactor, this system is applicable to a range of electron-rich aromatics and heteroaromatics. We also demonstrate the feasibility of C-H radiofluorination without an azeotropic drying step, which greatly simplifies the workflow of the labeling process.

Entities:  

Year:  2020        PMID: 33000949      PMCID: PMC7774802          DOI: 10.1021/acs.orglett.0c02815

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  17 in total

1.  Direct arene C-H fluorination with 18F- via organic photoredox catalysis.

Authors:  Wei Chen; Zeng Huang; Nicholas E S Tay; Benjamin Giglio; Mengzhe Wang; Hui Wang; Zhanhong Wu; David A Nicewicz; Zibo Li
Journal:  Science       Date:  2019-06-21       Impact factor: 47.728

2.  Predictive Model for Site-Selective Aryl and Heteroaryl C-H Functionalization via Organic Photoredox Catalysis.

Authors:  Kaila A Margrey; Joshua B McManus; Simone Bonazzi; Frederic Zecri; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2017-08-07       Impact factor: 15.419

3.  Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts.

Authors:  Tue B Petersen; Rehan Khan; Berit Olofsson
Journal:  Org Lett       Date:  2011-05-26       Impact factor: 6.005

4.  Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates.

Authors:  Sydonie D Schimler; Megan A Cismesia; Patrick S Hanley; Robert D J Froese; Matthew J Jansma; Douglas C Bland; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2017-01-23       Impact factor: 15.419

5.  Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride.

Authors:  Tobias L Ross; Johannes Ermert; Carsten Hocke; Heinz H Coenen
Journal:  J Am Chem Soc       Date:  2007-05-31       Impact factor: 15.419

6.  Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Authors:  Thanh Truong; Kristine Klimovica; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419

Review 7.  6-[18F]fluoro-L-DOPA: a well-established neurotracer with expanding application spectrum and strongly improved radiosyntheses.

Authors:  M Pretze; C Wängler; B Wängler
Journal:  Biomed Res Int       Date:  2014-05-28       Impact factor: 3.411

8.  Cu-Mediated C-H 18F-Fluorination of Electron-Rich (Hetero)arenes.

Authors:  Matthew S McCammant; Stephen Thompson; Allen F Brooks; Shane W Krska; Peter J H Scott; Melanie S Sanford
Journal:  Org Lett       Date:  2017-06-30       Impact factor: 6.005

9.  Concerted nucleophilic aromatic substitution with (19)F(-) and (18)F(-).

Authors:  Constanze N Neumann; Jacob M Hooker; Tobias Ritter
Journal:  Nature       Date:  2016-05-18       Impact factor: 49.962

10.  Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues.

Authors:  Angelika A Adamus-Grabicka; Magdalena Markowicz-Piasecka; Marcin Cieślak; Karolina Królewska-Golińska; Paweł Hikisz; Joachim Kusz; Magdalena Małecka; Elzbieta Budzisz
Journal:  Molecules       Date:  2020-04-01       Impact factor: 4.411

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  4 in total

1.  Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes.

Authors:  Jay S Wright; Liam S Sharninghausen; Sean Preshlock; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal:  J Am Chem Soc       Date:  2021-04-29       Impact factor: 15.419

Review 2.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

3.  SNAr Radiofluorination with In Situ Generated [18F]Tetramethylammonium Fluoride.

Authors:  So Jeong Lee; María T Morales-Colón; Allen F Brooks; Jay S Wright; Katarina J Makaravage; Peter J H Scott; Melanie S Sanford
Journal:  J Org Chem       Date:  2021-09-10       Impact factor: 4.198

Review 4.  Closing the gap between 19F and 18F chemistry.

Authors:  Javier Ajenjo; Gianluca Destro; Bart Cornelissen; Véronique Gouverneur
Journal:  EJNMMI Radiopharm Chem       Date:  2021-09-25
  4 in total

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