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Literature DB >> 26387796

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

Jian Zheng¹, Lu Wang², Jin-Hong Lin¹, Ji-Chang Xiao³, Steven H Liang⁴.

Abstract

The first trifluoromethylthiolation and [(18)F]trifluoromethylthiolation of alkyl electrophiles with in situ generated difluorocarbene in the presence of elemental sulfur and external (radioactive) fluoride ion is described. This transition-metal-free approach is high yielding, compatible with a variety of functional groups, and operated under mild reaction conditions. The conceptual advantage of this exogenous-fluoride-mediated transformation enables unprecedented syntheses of [(18)F]CF3S-labeled molecules from most commonly used [(18)F]fluoride ions. The rapid radiochemical reaction time (≤1 min) and high functional-group tolerance allow access to a variety of aliphatic [(18)F]CF3S compounds in high yields.

Entities: Chemical Disease Gene Species

Keywords: carbenes; fluorine; isotopic labeling; positron emission tomography; sulfur

Mesh：

Substances：

Year: 2015 PMID： 26387796 PMCID： PMC4692268 DOI： 10.1002/anie.201505446

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

65 in total

1. Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF3 and elemental sulfur.

Authors: Chao Chen; Yan Xie; Lingling Chu; Ruo-Wen Wang; Xingang Zhang; Feng-Ling Qing
Journal: Angew Chem Int Ed Engl Date: 2012-01-27 Impact factor: 15.336

2. Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent.

Authors: Iris Kieltsch; Patrick Eisenberger; Antonio Togni
Journal: Angew Chem Int Ed Engl Date: 2007 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. 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

5. Difluoromethylene phosphabetaine as an equivalent of difluoromethyl carbanion.

Authors: Vitalij V Levin; Alexey L Trifonov; Artem A Zemtsov; Marina I Struchkova; Dmitry E Arkhipov; Alexander D Dilman
Journal: Org Lett Date: 2014-11-25 Impact factor: 6.005

6. Direct dehydroxytrifluoromethylthiolation of alcohols using silver(I) trifluoromethanethiolate and tetra-n-butylammonium iodide.

Authors: Jian-Bo Liu; Xiu-Hua Xu; Zeng-Hao Chen; Feng-Ling Qing
Journal: Angew Chem Int Ed Engl Date: 2014-11-24 Impact factor: 15.336

7. Copper-catalyzed trifluoromethylthiolation of aryl halides with diverse directing groups.

Authors: Jiabin Xu; Xin Mu; Pinhong Chen; Jinxing Ye; Guosheng Liu
Journal: Org Lett Date: 2014-07-18 Impact factor: 6.005

8. A general copper-mediated nucleophilic 18F fluorination of arenes.

Authors: Matthew Tredwell; Sean M Preshlock; Nicholas J Taylor; Stefan Gruber; Mickael Huiban; Jan Passchier; Joël Mercier; Christophe Génicot; Véronique Gouverneur
Journal: Angew Chem Int Ed Engl Date: 2014-06-10 Impact factor: 15.336

9. Synthesis of gem-difluorocyclopropa(e)nes and O-, S-, N-, and P-difluoromethylated compounds with TMSCF(2)Br.

Authors: Lingchun Li; Fei Wang; Chuanfa Ni; Jinbo Hu
Journal: Angew Chem Int Ed Engl Date: 2013-09-12 Impact factor: 15.336

10. Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones.

Authors: Yupu Qiao; Tuda Si; Ming-Hsiu Yang; Ryan A Altman
Journal: J Org Chem Date: 2014-07-15 Impact factor: 4.354

10 in total

1. An Unconventional Mechanistic Insight into SCF₃ Formation from Difluorocarbene: Preparation of ¹⁸ F-Labeled α-SCF₃ Carbonyl Compounds.

Authors: Jian Zheng; Ran Cheng; Jin-Hong Lin; Dong-Hai Yu; Longle Ma; Lina Jia; Lan Zhang; Lu Wang; Ji-Chang Xiao; Steven H Liang
Journal: Angew Chem Int Ed Engl Date: 2017-02-14 Impact factor: 15.336

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

Authors: Hang Shi; Augustin Braun; Lu Wang; Steven H Liang; Neil Vasdev; Tobias Ritter
Journal: Angew Chem Int Ed Engl Date: 2016-08-05 Impact factor: 15.336

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

Review 4. Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

Authors: Yunze Wang; Qingyu Lin; Hongcheng Shi; Dengfeng Cheng
Journal: Front Chem Date: 2022-06-29 Impact factor: 5.545

5. Synthesis of enantiopure ¹⁸F-trifluoromethyl cysteine as a structure-mimetic amino acid tracer for glioma imaging.

Authors: Shaoyu Liu; Hui Ma; Zhanwen Zhang; Liping Lin; Gongjun Yuan; Xiaolan Tang; Dahong Nie; Shende Jiang; Guang Yang; Ganghua Tang
Journal: Theranostics Date: 2019-01-30 Impact factor: 11.556

6. ¹⁸F-Trifluoromethanesulfinate Enables Direct C-H ¹⁸F-Trifluoromethylation of Native Aromatic Residues in Peptides.

Authors: Choon Wee Kee; Osman Tack; Florian Guibbal; Thomas C Wilson; Patrick G Isenegger; Mateusz Imiołek; Stefan Verhoog; Michael Tilby; Giulia Boscutti; Sharon Ashworth; Juliette Chupin; Roxana Kashani; Adeline W J Poh; Jane K Sosabowski; Sven Macholl; Christophe Plisson; Bart Cornelissen; Michael C Willis; Jan Passchier; Benjamin G Davis; Véronique Gouverneur
Journal: J Am Chem Soc Date: 2020-01-13 Impact factor: 15.419

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

1. Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF3 and elemental sulfur.

2. Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent.

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

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

5. Difluoromethylene phosphabetaine as an equivalent of difluoromethyl carbanion.

6. Direct dehydroxytrifluoromethylthiolation of alcohols using silver(I) trifluoromethanethiolate and tetra-n-butylammonium iodide.

7. Copper-catalyzed trifluoromethylthiolation of aryl halides with diverse directing groups.

8. A general copper-mediated nucleophilic 18F fluorination of arenes.

9. Synthesis of gem-difluorocyclopropa(e)nes and O-, S-, N-, and P-difluoromethylated compounds with TMSCF(2)Br.

10. Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones.

1. An Unconventional Mechanistic Insight into SCF₃ Formation from Difluorocarbene: Preparation of ¹⁸ F-Labeled α-SCF₃ Carbonyl Compounds.

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

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

Review 4. Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

5. Synthesis of enantiopure ¹⁸F-trifluoromethyl cysteine as a structure-mimetic amino acid tracer for glioma imaging.

6. ¹⁸F-Trifluoromethanesulfinate Enables Direct C-H ¹⁸F-Trifluoromethylation of Native Aromatic Residues in Peptides.

Review 7. Advances in [¹⁸F]Trifluoromethylation Chemistry for PET Imaging.

Review 8. Recent Advances in Synthetic Methodologies to Form C-¹⁸F Bonds.

9. Rapid Dehydroxytrifluoromethoxylation of Alcohols.

Review 10. Closing the gap between ¹⁹F and ¹⁸F chemistry.

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

Review 4. Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

Review 7. Advances in [18F]Trifluoromethylation Chemistry for PET Imaging.

Review 8. Recent Advances in Synthetic Methodologies to Form C-18F Bonds.

Review 10. Closing the gap between 19F and 18F chemistry.

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

Review 7. Advances in [¹⁸F]Trifluoromethylation Chemistry for PET Imaging.

Review 8. Recent Advances in Synthetic Methodologies to Form C-¹⁸F Bonds.

Review 10. Closing the gap between ¹⁹F and ¹⁸F chemistry.