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Literature DB >> 27491349

Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

Hang Shi^1,2, Augustin Braun¹, Lu Wang², Steven H Liang^3,4, Neil Vasdev^5,6, Tobias Ritter^7,8,9.

Abstract

A general method for the synthesis of [(18) F]difluoromethylarenes from [(18) F]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 (18) F-fluorination precursors are readily prepared from aryl chlorides, bromides, iodides, and triflates. Seven (18) F-difluoromethylarene drug analogues and radiopharmaceuticals including Claritin, fluoxetine (Prozac), and [(18) F]DAA1106 were synthesized to show the potential of the method for applications in PET radiopharmaceutical design.

Entities: Chemical Species

Keywords: aryl (pseudo) halides; difluoromethylarenes; fluorine-18; positron emission tomography; radiopharmaceuticals

Mesh：

Substances：

Year: 2016 PMID： 27491349 PMCID： PMC5189681 DOI： 10.1002/anie.201604106

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

32 in total

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Journal: Br J Clin Pharmacol Date: 2012-02 Impact factor: 4.335

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Authors: Philip W Miller; Nicholas J Long; Ramon Vilar; Antony D Gee
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Cu(I)-mediated (18)F-trifluoromethylation of arenes: rapid synthesis of (18)F-labeled trifluoromethyl arenes.

Authors: T Rühl; W Rafique; V T Lien; P J Riss
Journal: Chem Commun (Camb) Date: 2014-04-28 Impact factor: 6.222

4. A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging.

Authors: Mickael Huiban; Matthew Tredwell; Satoshi Mizuta; Zehong Wan; Xiaomin Zhang; Thomas Lee Collier; Véronique Gouverneur; Jan Passchier
Journal: Nat Chem Date: 2013-09-08 Impact factor: 24.427

5. Targeted fluorination with the fluoride ion by manganese-catalyzed decarboxylation.

Authors: Xiongyi Huang; Wei Liu; Jacob M Hooker; John T Groves
Journal: Angew Chem Int Ed Engl Date: 2015-03-03 Impact factor: 15.336

6. 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

7. Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

Authors: Jian Zheng; Lu Wang; Jin-Hong Lin; Ji-Chang Xiao; Steven H Liang
Journal: Angew Chem Int Ed Engl Date: 2015-09-21 Impact factor: 15.336

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

Review 9. Clinical applications of PET in oncology.

Authors: Eric M Rohren; Timothy G Turkington; R Edward Coleman
Journal: Radiology Date: 2004-03-24 Impact factor: 11.105

10. Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids.

Authors: Andrew V Mossine; Allen F Brooks; Katarina J Makaravage; Jason M Miller; Naoko Ichiishi; Melanie S Sanford; Peter J H Scott
Journal: Org Lett Date: 2015-11-14 Impact factor: 6.005

7 in total

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

Authors: Xiaojun Zeng; Junling Li; Chin K Ng; Gerald B Hammond; Bo Xu
Journal: Angew Chem Int Ed Engl Date: 2018-02-13 Impact factor: 15.336

2. A Facile Radiolabeling of [¹⁸F]FDPA via Spirocyclic Iodonium Ylides: Preliminary PET Imaging Studies in Preclinical Models of Neuroinflammation.

Authors: Lu Wang; Ran Cheng; Masayuki Fujinaga; Jian Yang; Yiding Zhang; Akiko Hatori; Katsushi Kumata; Jing Yang; Neil Vasdev; Yunfei Du; Chongzhao Ran; Ming-Rong Zhang; Steven H Liang
Journal: J Med Chem Date: 2017-06-05 Impact factor: 7.446

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

Authors: Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal: Angew Chem Int Ed Engl Date: 2019-01-14 Impact factor: 15.336

4. Late-Stage ¹⁸ F-Difluoromethyl Labeling of N-Heteroaromatics with High Molar Activity for PET Imaging.

Authors: Laura Trump; Agostinho Lemos; Bénédicte Lallemand; Patrick Pasau; Joël Mercier; Christian Lemaire; André Luxen; Christophe Genicot
Journal: Angew Chem Int Ed Engl Date: 2019-08-09 Impact factor: 15.336

5. Direct C-H difluoromethylation of heterocycles via organic photoredox catalysis.

Authors: Wei Zhang; Xin-Xin Xiang; Junyi Chen; Chen Yang; Yu-Liang Pan; Jin-Pei Cheng; Qingbin Meng; Xin Li
Journal: Nat Commun Date: 2020-01-31 Impact factor: 14.919

6. Easily automated radiosynthesis of [¹⁸F]P10A-1910 and its clinical translation to quantify phosphodiesterase 10A in human brain.

Authors: Huiyi Wei; Junjie Wei; Shaojuan Zhang; Shiliang Dong; Guocong Li; Wenqing Ran; Chenchen Dong; Weibin Zhang; Chao Che; Wenzhao Luo; Hao Xu; Zhiyong Dong; Jinghao Wang; Lu Wang
Journal: Front Bioeng Biotechnol Date: 2022-09-06

Review 7. 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