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References (64)
-
K. Niedermann, Natalja Früh, R. Senn, Barbara Czarniecki, R. Verel, A. Togni (2012)
Direct electrophilic N-trifluoromethylation of azoles by a hypervalent iodine reagent.Angewandte Chemie, 51 26
-
I. Ruppert, Klaus Schlich, W. Volbach (1984)
Die ersten CF3-substituierten organyl(chlor)silaneTetrahedron Letters, 25
-
J. Nie, Hong-Chao Guo, D. Cahard, Jun‐An Ma (2011)
Asymmetric construction of stereogenic carbon centers featuring a trifluoromethyl group from prochiral trifluoromethylated substrates.Chemical reviews, 111 2
-
K. Aikawa, Wataru Toya, Yuzo Nakamura, K. Mikami (2015)
Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources.Organic letters, 17 20
-
Zhonglin Liu, Haiwen Xiao, Benxiang Zhang, Haigen Shen, Lin Zhu, Chaozhong Li (2019)
Copper-Catalyzed Remote C(sp3 )-H Trifluoromethylation of Carboxamides and Sulfonamides.Angewandte Chemie, 58 8
-
K. Kanie, K. Mizuno, M. Kuroboshi*, T. Hiyama (1998)
A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates.Bulletin of the Chemical Society of Japan, 71
-
Xinting Yuan, Kun Liu, Chaozhong Li (2008)
Development of highly regioselective amidyl radical cyclization based on lone pair-lone pair repulsion.The Journal of organic chemistry, 73 16
-
Lin Zhu, Yewen Fang, Chaozhong Li (2020)
Trifluoromethylation of Alkyl Radicals: Breakthrough and Challenges †Chinese Journal of Chemistry, 38
-
Xinqiang Tan, Zhonglin Liu, Haigen Shen, Pei Zhang, Zhenzhen Zhang, Chaozhong Li (2017)
Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids.Journal of the American Chemical Society, 139 36
-
Matthew Paeth, William Carson, Jheng-hua Luo, D. Tierney, Z. Cao, M. Cheng, Wei Liu (2018)
Copper-Mediated Trifluoromethylation of Benzylic Csp3 -H Bonds.Chemistry, 24 45
-
L. Markovskij, V. Pashinnik, A. Kirsanov (1973)
Application of Dialkylaminosulfur Trifluorides in the Synthesis of Fluoroorganic CompoundsSynthesis, 1973
-
Qiqiang Xie, Jinbo Hu (2020)
Chen's Reagent: A Versatile Reagent for Trifluoromethylation, Difluoromethylenation, and Difluoroalkylation in Organic Synthesis †Chinese Journal of Chemistry, 38
-
K. Niedermann, Natalja Früh, E. Vinogradova, Matthias Wiehn, A. Moreno, A. Togni (2011)
A Ritter-type reaction: direct electrophilic trifluoromethylation at nitrogen atoms using hypervalent iodine reagents.Angewandte Chemie, 50 5
-
T. Umemoto, K. Adachi, S. Ishihara (2007)
CF3 oxonium salts, O-(trifluoromethyl)dibenzofuranium salts: in situ synthesis, properties, and application as a real CF3+ species reagent.The Journal of organic chemistry, 72 18
-
M. Kuroboshi*, T. Hiyama (1992)
A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamatesTetrahedron Letters, 33
-
Youlia Hagooly, S. Rozen (2012)
Pyridine•BrF3, the missing link for clean fluorinations of aromatic derivatives.Organic letters, 14 4
-
R. Singh, J. Shreeve (2004)
Recent highlights in electrophilic fluorination with 1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate).Accounts of chemical research, 37 1
-
C. Alonso, Eduardo Marigorta, Gloria Rubiales, F. Palacios (2015)
Carbon trifluoromethylation reactions of hydrocarbon derivatives and heteroarenes.Chemical reviews, 115 4
-
E. Klauke (1966)
Preparation and Properties of Substances with N‐ or S‐Perhalogenomethyl GroupsAngewandte Chemie, 5
-
Jian-Bo Liu, Xiuhua Xu, F. Qing (2015)
Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers.Organic letters, 17 20
-
K. Sahu, V. Ravichandran, V. Mourya, R. Agrawal (2007)
QSAR analysis of caffeoyl naphthalene sulfonamide derivatives as HIV-1 integrase inhibitorsMedicinal Chemistry Research, 15
-
Hongjian Lu, Qian Chen, Chaozhong Li (2007)
Control of the regioselectivity of sulfonamidyl radical cyclization by vinylic halogen substitution.The Journal of organic chemistry, 72 7
-
T. Abe, E. Hayashi, H. Baba, H. Fukaya (1990)
The electrochemical fluorination of nitrogen-containing carboxylic acids. Fluorination of dimethylamino- or diethylamino-substituted carboxylic acid derivativesJournal of Fluorine Chemistry, 48
-
Zhenzhen Zhang, Lin Zhu, Chaozhong Li (2019)
Copper‐Catalyzed Carbotrifluoromethylation of Unactivated Alkenes Driven by Trifluoromethylation of Alkyl RadicalsChinese Journal of Chemistry
-
N. Shibata, Andrej Matsnev, D. Cahard (2010)
Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspectiveBeilstein Journal of Organic Chemistry, 6
-
E. Merino, C. Nevado (2014)
Addition of CF3 across unsaturated moieties: a powerful functionalization toolChemical Society Reviews, 43
-
Tianshun Hu, Kun Liu, M. Shen, Xinting Yuan, Yu Tang, Chaozhong Li (2007)
O-attack versus N-attack: electrophilic halocyclization of unsaturated amides with vinylic halogen substitution.The Journal of organic chemistry, 72 22
-
Zhaodong Li, Zhentao Wang, Lin Zhu, Xinqiang Tan, Chaozhong Li (2014)
Silver-catalyzed radical fluorination of alkylboronates in aqueous solution.Journal of the American Chemical Society, 136 46
-
Zhaodong Li, Liyan Song, Chaozhong Li (2013)
Silver-catalyzed radical aminofluorination of unactivated alkenes in aqueous media.Journal of the American Chemical Society, 135 12
-
R. Eujen, B. Hoge, D. Brauer (1997)
Preparation and NMR Spectra of the (Trifluoromethyl)argentates(III) [Ag(CF3)nX4-n]-, with X = CN (n = 1−3), CH3, C⋮CC6H11, Cl, Br (n = 2, 3), and I (n = 3), and of Related Silver(III) Compounds. Structures of [PPh4][trans-Ag(CF3)2(CN)2] and [PPh4][Ag(CF3)3(CH3)]†Inorganic Chemistry, 36
-
Haigen Shen, Zhonglin Liu, Pei Zhang, Xinqiang Tan, Zhenzhen Zhang, Chaozhong Li (2017)
Trifluoromethylation of Alkyl Radicals in Aqueous Solution.Journal of the American Chemical Society, 139 29
-
Tianshun Hu, M. Shen, Qian Chen, Chaozhong Li (2006)
Pushing radical cyclization from regioselective to regiospecific: cyclization of amidyl radicals controlled by vinylic halogen substitution.Organic letters, 8 12
-
Shuo Guo, Deyaa AbuSalim, S. Cook (2018)
Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.Journal of the American Chemical Society, 140 39
-
Andrew Romine, N. Nebra, A. Konovalov, E. Martín, J. Benet‐Buchholz, V. Grushin (2015)
Easy access to the copper(III) anion [Cu(CF3 )4 ](-).Angewandte Chemie, 54 9
-
T. Koike, M. Akita (2016)
Fine Design of Photoredox Systems for Catalytic Fluoromethylation of Carbon-Carbon Multiple Bonds.Accounts of chemical research, 49 9
-
F. Yin, Zhentao Wang, Zhaodong Li, Chaozhong Li (2012)
Silver-catalyzed decarboxylative fluorination of aliphatic carboxylic acids in aqueous solution.Journal of the American Chemical Society, 134 25
-
N. Shibata, S. Mizuta, Hiroyuki Kawai (2008)
Recent advances in enantioselective trifluoromethylation reactionsTetrahedron-asymmetry, 19
-
J. Charpentier, Natalja Früh, A. Togni (2015)
Electrophilic trifluoromethylation by use of hypervalent iodine reagents.Chemical reviews, 115 2
-
M. Schlosser (2006)
CF(3)-bearing aromatic and heterocyclic building blocks.Angewandte Chemie, 45 33
-
T. Koike, M. Akita (2014)
Trifluoromethylation by Visible-Light-Driven Photoredox CatalysisTopics in Catalysis, 57
-
R. Harder, W. Smith (1961)
Chemistry of Sulfur Tetrafluoride.1 VI. Fluorination of Thiocarbonyl CompoundsJournal of the American Chemical Society, 83
-
Wieland Tyrra (2001)
Die Desulfonierung–Fluorierung von Thiuramdisulfiden, [R2NC(S)S]2 und Silberdithiocarbamaten, Ag[SC(S)NR2] (R = CH3, CH3CH2, C6H5CH2), mit Silber(I)fluorid, AgF — ein einfacher Zugang zu Diorgano(trifluormethyl)aminen, R2NCF3, und Thiocarbamoylfluoriden, R2NC(S)FJournal of Fluorine Chemistry, 109
-
R. Banks, Suad Mohialdin-Khaffaf, G. Lal, I. Sharif, R. Syvret (1992)
1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts: a novel family of electrophilic fluorinating agentsJournal of The Chemical Society, Chemical Communications
-
Fan Teng, Jiang Cheng, C. Bolm (2015)
Silver-Mediated N-Trifluoromethylation of Sulfoximines.Organic letters, 17 12
-
Youlia Hagooly, Julia Gatenyo, A. Hagooly, S. Rozen (2009)
Toward the synthesis of the rare N-(trifluoromethyl)amides and the N-(difluoromethylene)-N-(trifluoromethyl)amines [RN(CF3)CF2R'] using BrF3.The Journal of organic chemistry, 74 22
-
Jian-Bo Liu, Chaoyue Chen, L. Chu, Zeng-Hao Chen, Xiuhua Xu, F. Qing (2015)
Silver-Mediated Oxidative Trifluoromethylation of Phenols: Direct Synthesis of Aryl Trifluoromethyl Ethers.Angewandte Chemie, 54 40
-
G. Pawelke (1991)
Reaction of tetrakis(dimethylamino)ethylene with CF2Br2 in the presence of secondary amines, formation of N-trifluoromethyl-dialkylaminesJournal of Fluorine Chemistry, 52
-
W. Tyrra, D. Naumann (2004)
Perfluoroorganosilver(I) CompoundsChemInform, 35
-
T. Liang, Constanze Neumann, T. Ritter (2013)
Introduction of fluorine and fluorine-containing functional groups.Angewandte Chemie, 52 32
-
P. Nyffeler, S. Durón, M. Burkart, S. Vincent, Chi‐Huey Wong (2004)
Selectfluor: mechanistic insight and applications.Angewandte Chemie, 44 2
-
Daniel Joven‐Sancho, M. Baya, Antonio Martín, B. Menjón (2018)
Homoleptic Trifluoromethyl Derivatives of AgI and AgIII.Chemistry
-
Haiwen Xiao, Zhonglin Liu, Haigen Shen, Benxiang Zhang, Lin Zhu, Chaozhong Li (2019)
Copper-Catalyzed Late-Stage Benzylic C(sp3)–H TrifluoromethylationChem
-
Haiwen Xiao, Haigen Shen, Lin Zhu, Chaozhong Li (2019)
Copper-Catalyzed Radical Aminotrifluoromethylation of Alkenes.Journal of the American Chemical Society
-
T. Scattolin, Kristina Deckers, Franziska Schoenebeck (2016)
Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench‐Stable Precursor (Me4N)SCF3Angewandte Chemie (International Ed. in English), 56
-
W. Dmowski, M. Kamiński (1983)
Reaction of tertiary formamides with sulphur tetrafluoride. Direct synthesis of (trifluoromethyl)aminesJournal of Fluorine Chemistry, 23
-
G. Zheng, Xiaoli Ma, Jiaheng Li, Dongsheng Zhu, Mang Wang (2015)
Electrophilic N-Trifluoromethylation of N-H Ketimines.The Journal of organic chemistry, 80 17
-
T. Scattolin, Samir Bouayad‐Gervais, Franziska Schoenebeck (2019)
Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureasNature, 573
-
Chengwei Zhang, Zhaodong Li, Lin Zhu, Limei Yu, Zhentao Wang, Chaozhong Li (2013)
Silver-catalyzed radical phosphonofluorination of unactivated alkenes.Journal of the American Chemical Society, 135 38
-
E. Differding, H. Ofner (1991)
N-Fluorobenzenesulfonimide: A Practical Reagent For Electrophilic FluorinationsSynlett, 1991
-
H. Egami, M. Sodeoka (2014)
Trifluoromethylation of alkenes with concomitant introduction of additional functional groups.Angewandte Chemie, 53 32
-
G. Prakash, Ramesh Krishnamurti, G. Olah (1989)
Synthetic methods and reactions. 141. Fluoride-induced trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane (TMS-CF3). A trifluoromethide equivalentJournal of the American Chemical Society, 111
-
R. J. Harder, W. C. Smith, L. N. Markovskij, V. E. Pashinnik, A. V. Kirsanov, M. Kuroboshi, T. Hiyama, K. Kanie, K. Mizuno, M. Kuroboshi, T. Hiyama, W. Tyrra, Y. Hagooly, S. Rozen, J. Yu, J.‐H. Lin, J.‐C. Xiao, T. Scattolin, K. Deckers, F. Schoenebeck (1961)
Chemistry of Sulfur Tetrafluoride, 83
-
Jiao Yu, Jin‐Hong Lin, Ji-Chang Xiao (2017)
Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines.Angewandte Chemie, 56 52
-
A. Studer (2012)
A "Renaissance" in radical trifluoromethylation.Angewandte Chemie, 51 36
- Publisher
- Wiley
- Copyright
- © 2020 SIOC, CAS, Shanghai & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 1001-604X
- eISSN
- 1614-7065
- DOI
- 10.1002/cjoc.202000132
- Publisher site
- See Article on Publisher Site
Abstract
We report herein the direct N‐trifluoromethylation of N‐H amides. Promoted by AgOTf and 2‐fluoropyridine, the reaction of a variety of amides with Selectfluor, TMSCF3 and CsF proceeds smoothly at room temperature leading to the corresponding N‐trifluoromethylated products in satisfactory yields. The protocol is also applicable to amino acid derivatives, resulting in efficient and chemoselective N‐trifluoromethylation of di‐ and tri‐peptides with retention of configuration. A mechanism involving reductive elimination of Ag(III) intermediates to form N—CF3 bonds is proposed.
Journal
Chinese Journal of Chemistry – Wiley
Published: Sep 1, 2020
Keywords: ; ; ; ;