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Literature DB >> 28194833

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

Jian Zheng¹, Ran Cheng^2,3, Jin-Hong Lin¹, Dong-Hai Yu¹, Longle Ma³, Lina Jia⁴, Lan Zhang⁴, Lu Wang³, Ji-Chang Xiao¹, Steven H Liang³.

Abstract

Trifluoromethylthiolation by sulfuration of difluorocarbene with elemental sulfur is described for the first time, which overrides long-standing trifluoromethyl anion-based theory. Mechanistic elucidation reveals an unprecedented chemical process for the formation of thiocarbonyl fluoride and also enables transition-metal-mediated trifluoromethylthiolation and [18 F]trifluoromethylthiolation of α-bromo carbonyl compounds with broad substrate scope and compatibility.

Entities: CellLine Chemical Disease Gene

Keywords: 18F-labeling; difluorocarbene; fluorine; sulfuration; trifluoromethylthiolation

Year: 2017 PMID： 28194833 PMCID： PMC5582945 DOI： 10.1002/anie.201611761

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

30 in total

1. Fluorinated Ylides and Related Compounds.

Authors: Donald J. Burton; Zhen-Yu Yang; Weiming Qiu
Journal: Chem Rev Date: 1996-08-01 Impact factor: 60.622

2. Synthesis of 3-fluoroalkenyl-3-trifluoromethyl-2-oxindoles by the reaction of indoline-2,3-diones with difluoromethylene phosphabetaine.

Authors: Yingle Liu; Ke Zhang; Yangen Huang; Shen Pan; Xiao-Qiang Liu; Yi Yang; Yan Jiang; Xiu-Hua Xu
Journal: Chem Commun (Camb) Date: 2016-04-08 Impact factor: 6.222

3. Selective difluoromethylation and monofluoromethylation reactions.

Authors: Jinbo Hu; Wei Zhang; Fei Wang
Journal: Chem Commun (Camb) Date: 2009-10-30 Impact factor: 6.222

4. Long-lived trifluoromethanide anion: a key intermediate in nucleophilic trifluoromethylations.

Authors: G K Surya Prakash; Fang Wang; Zhe Zhang; Ralf Haiges; Martin Rahm; Karl O Christe; Thomas Mathew; George A Olah
Journal: Angew Chem Int Ed Engl Date: 2014-08-21 Impact factor: 15.336

5. 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

6. 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

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. Difluorocarbene Addition to Alkenes and Alkynes in Continuous Flow.

Authors: Pauline Rullière; Patrick Cyr; André B Charette
Journal: Org Lett Date: 2016-04-27 Impact factor: 6.005

9. Pd-Catalyzed Transfer of Difluorocarbene.

Authors: Xiao-Yun Deng; Jin-Hong Lin; Ji-Chang Xiao
Journal: Org Lett Date: 2016-08-12 Impact factor: 6.005

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

12 in total

Review 1. 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 2. 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

3. Copper-Mediated Late-stage Radiofluorination: Five Years of Impact on Pre-clinical and Clinical PET Imaging.

Authors: Jay S Wright; Tanpreet Kaur; Sean Preshlock; Sean S Tanzey; Wade P Winton; Liam S Sharninghausen; Nicholas Wiesner; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal: Clin Transl Imaging Date: 2020-05-26

4. Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters.

Authors: Liyin Jiang; Pau Sarró; Wei Jie Teo; Jordi Llop; Marcos G Suero
Journal: Chem Sci Date: 2022-03-15 Impact factor: 9.825

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. Chlorodifluoromethane as a C1 Synthon in the Assembly of N-Containing Compounds.

Authors: Xingxing Ma; Jianke Su; Xingang Zhang; Qiuling Song
Journal: iScience Date: 2019-07-08

7. S₈-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles.

Authors: Shuilin Deng; Haohua Chen; Xingxing Ma; Yao Zhou; Kai Yang; Yu Lan; Qiuling Song
Journal: Chem Sci Date: 2019-06-05 Impact factor: 9.825

8. 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

9. Rapid Dehydroxytrifluoromethoxylation of Alcohols.

Authors: Wei Zhang; Jia Chen; Jin-Hong Lin; Ji-Chang Xiao; Yu-Cheng Gu
Journal: iScience Date: 2018-07-11

Review 10. 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

Review 1. Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Review 2. Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

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

Review 1. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

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