Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
Abstract
A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rates of the reactions. Interestingly, differences in reactivity were observed when a well-defined [LCuCF3] complex was employed directly or generated in situ from precursors by published reports. Relative reactivities were also found to highly dependent on the nature of the iodoarenes.
- Authors:
-
- Lehigh Univ., Bethlehem, PA (United States). Dept. of Chemistry
- Publication Date:
- Research Org.:
- Lehigh Univ., Bethlehem, PA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1502977
- Grant/Contract Number:
- SC0009363
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Beilstein Journal of Organic Chemistry
- Additional Journal Information:
- Journal Volume: 13; Journal ID: ISSN 1860-5397
- Publisher:
- Beilstein-Institut
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; benchmarking; copper; fluorine; fluoroalkylation; trifluoromethylation
Citation Formats
Kaplan, Peter T., Lloyd, Jessica A., Chin, Mason T., and Vicic, David A. Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides. United States: N. p., 2017.
Web. doi:10.3762/bjoc.13.225.
Kaplan, Peter T., Lloyd, Jessica A., Chin, Mason T., & Vicic, David A. Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides. United States. https://doi.org/10.3762/bjoc.13.225
Kaplan, Peter T., Lloyd, Jessica A., Chin, Mason T., and Vicic, David A. Mon .
"Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides". United States. https://doi.org/10.3762/bjoc.13.225. https://www.osti.gov/servlets/purl/1502977.
@article{osti_1502977,
title = {Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides},
author = {Kaplan, Peter T. and Lloyd, Jessica A. and Chin, Mason T. and Vicic, David A.},
abstractNote = {A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rates of the reactions. Interestingly, differences in reactivity were observed when a well-defined [LCuCF3] complex was employed directly or generated in situ from precursors by published reports. Relative reactivities were also found to highly dependent on the nature of the iodoarenes.},
doi = {10.3762/bjoc.13.225},
journal = {Beilstein Journal of Organic Chemistry},
number = ,
volume = 13,
place = {United States},
year = {Mon Oct 30 00:00:00 EDT 2017},
month = {Mon Oct 30 00:00:00 EDT 2017}
}
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Cited by: 6 works
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Figures / Tables:
Scheme 1: Reagents and precursors used for trifluoromethylation reactions.
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Works referenced in this record:
Aromatic Trifluoromethylation with Metal Complexes
journal, August 2011
- Tomashenko, Olesya A.; Grushin, Vladimir V.
- Chemical Reviews, Vol. 111, Issue 8
Organometallic Aspects of Fluoroalkylation Reactions with Copper and Nickel
journal, August 2013
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journal, July 2012
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Cooperative Effect of Silver in Copper-Catalyzed Trifluoromethylation of Aryl Iodides Using Me 3 SiCF 3
journal, June 2011
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Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide
journal, January 2013
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Copper-Catalyzed Trifluoromethylation of Aryl Iodides with Potassium (Trifluoromethyl)trimethoxyborate
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journal, January 1989
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Structure of Bis(trifluoromethyl)cuprate and Its Role in Trifluoromethylation Reactions
journal, December 2008
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Active Trifluoromethylating Agents from Well-Defined Copper(I)−CF 3 Complexes
journal, July 2008
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- Journal of the American Chemical Society, Vol. 130, Issue 27
A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides
journal, March 2011
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CSi bond cleavage of trihalomethyltrimethylsilane by alkoxo- and aryloxogold or -copper complexes
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journal, June 2011
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Mechanism of Trifluoromethylation of Aryl Halides with CuCF 3 and the Ortho Effect
journal, September 2014
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- Journal of the American Chemical Society, Vol. 136, Issue 38
Toward Benchmarking in Catalysis Science: Best Practices, Challenges, and Opportunities
journal, March 2016
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- ACS Catalysis, Vol. 6, Issue 4
A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides
journal, March 2011
- Morimoto, Hiroyuki; Tsubogo, Tetsu; Litvinas, Nichole D.
- Angewandte Chemie International Edition, Vol. 50, Issue 16
Simple, Stable, and Easily Accessible Well-Defined CuCF3 Aromatic Trifluoromethylating Agents
journal, June 2011
- Tomashenko, Olesya A.; Escudero-Adán, Eduardo C.; Martínez Belmonte, Marta
- Angewandte Chemie International Edition, Vol. 50, Issue 33
Copper-Catalyzed Trifluoromethylation of Aryl Iodides with Potassium (Trifluoromethyl)trimethoxyborate
journal, January 2011
- Knauber, Thomas; Arikan, Fatih; Röschenthaler, Gerd-Volker
- Chemistry - A European Journal, Vol. 17, Issue 9
Towards a Practical and Efficient Copper-Catalyzed Trifluoromethylation of Aryl Halides
journal, July 2012
- Schareina, Thomas; Wu, Xiao-Feng; Zapf, Alexander
- Topics in Catalysis, Vol. 55, Issue 7-10
Trifluoromethylation of aryl and heteroaryl halides
journal, March 2011
- Roy, Sudipta; Gregg, Brian T.; Gribble, Gordon W.
- Tetrahedron, Vol. 67, Issue 12
Toward Benchmarking in Catalysis Science: Best Practices, Challenges, and Opportunities
journal, March 2016
- Bligaard, Thomas; Bullock, R. Morris; Campbell, Charles T.
- ACS Catalysis, Vol. 6, Issue 4
Aromatic Trifluoromethylation with Metal Complexes
journal, August 2011
- Tomashenko, Olesya A.; Grushin, Vladimir V.
- Chemical Reviews, Vol. 111, Issue 8
Mechanism of Trifluoromethylation of Aryl Halides with CuCF 3 and the Ortho Effect
journal, September 2014
- Konovalov, Andrey I.; Lishchynskyi, Anton; Grushin, Vladimir V.
- Journal of the American Chemical Society, Vol. 136, Issue 38
Active Trifluoromethylating Agents from Well-Defined Copper(I)−CF 3 Complexes
journal, July 2008
- Dubinina, Galyna G.; Furutachi, Hideki; Vicic, David A.
- Journal of the American Chemical Society, Vol. 130, Issue 27
Cooperative Effect of Silver in Copper-Catalyzed Trifluoromethylation of Aryl Iodides Using Me 3 SiCF 3
journal, June 2011
- Weng, Zhiqiang; Lee, Richmond; Jia, Weiguo
- Organometallics, Vol. 30, Issue 11
Structure of Bis(trifluoromethyl)cuprate and Its Role in Trifluoromethylation Reactions
journal, December 2008
- Dubinina, Galyna G.; Ogikubo, Junichi; Vicic, David A.
- Organometallics, Vol. 27, Issue 23
Methyl fluorosulphonyldifluoroacetate; a new trifluoromethylating agent
journal, January 1989
- Chen, Qing-Yun; Wu, Sheng-Wen
- Journal of the Chemical Society, Chemical Communications, Issue 11
Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide
journal, January 2013
- Nakamura, Yuzo; Fujiu, Motohiro; Murase, Tatsuya
- Beilstein Journal of Organic Chemistry, Vol. 9
Works referencing / citing this record:
Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides
journal, March 2018
- Keaveney, Sinead T.; Schoenebeck, Franziska
- Angewandte Chemie, Vol. 130, Issue 15
Exploring the Role of Coinage Metalates in Trifluoromethylation: A Combined Experimental and Theoretical Study
journal, March 2019
- Martínez de Salinas, Sara; Mudarra, Ángel L.; Odena, Carlota
- Chemistry – A European Journal, Vol. 25, Issue 40
Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides
journal, March 2018
- Keaveney, Sinead T.; Schoenebeck, Franziska
- Angewandte Chemie International Edition, Vol. 57, Issue 15
Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides
journal, March 2018
- Keaveney, Sinead T.; Schoenebeck, Franziska
- Angewandte Chemie International Edition, Vol. 57, Issue 15
Figures / Tables found in this record:
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.