Deoxytrifluoromethylation of Alcohols

Intermaggio, Nicholas E.; Millet, Agustin; Davis, Dali L.; MacMillan, David W.  C.

doi:10.1021/jacs.2c04807

Deoxytrifluoromethylation of Alcohols

Journal Article · 05 July 2022 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c04807· OSTI ID:1978492

Intermaggio, Nicholas E. ^[1]; ^[1]; Davis, Dali L. ^[1]; MacMillan, David W. C. ^[1]

Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States

Not provided.

Research Organization:: Princeton Univ., NJ (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0019370

OSTI ID:: 1978492

Journal Information:: Journal of the American Chemical Society, Vol. 144, Issue 27; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (50)

Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?: Miniperspective Brown, Dean G.; Boström, Jonas Journal of Medicinal Chemistry, Vol. 59, Issue 10 https://doi.org/10.1021/acs.jmedchem.5b01409	journal	December 2015
What Do Medicinal Chemists Actually Make? A 50-Year Retrospective Walters, W. Patrick; Green, Jeremy; Weiss, Jonathan R. Journal of Medicinal Chemistry, Vol. 54, Issue 19 https://doi.org/10.1021/jm200504p	journal	August 2011
What is in Our Kit? An Analysis of Building Blocks Used in Medicinal Chemistry Parallel Libraries Wang, Ying; Haight, Isabella; Gupta, Rishi Journal of Medicinal Chemistry, Vol. 64, Issue 23 https://doi.org/10.1021/acs.jmedchem.1c01139	journal	November 2021
Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success Lovering, Frank; Bikker, Jack; Humblet, Christine Journal of Medicinal Chemistry, Vol. 52, Issue 21 https://doi.org/10.1021/jm901241e	journal	November 2009
Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp ² )–C(sp ³ ) Cross-Coupling Methods by Library Synthesis Dombrowski, Amanda W.; Gesmundo, Nathan J.; Aguirre, Ana L. ACS Medicinal Chemistry Letters, Vol. 11, Issue 4 https://doi.org/10.1021/acsmedchemlett.0c00093	journal	March 2020
Organic synthesis provides opportunities to transform drug discovery Blakemore, David C.; Castro, Luis; Churcher, Ian Nature Chemistry, Vol. 10, Issue 4 https://doi.org/10.1038/s41557-018-0021-z	journal	March 2018
Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design Meanwell, Nicholas A. Journal of Medicinal Chemistry, Vol. 61, Issue 14 https://doi.org/10.1021/acs.jmedchem.7b01788	journal	February 2018
The Many Roles for Fluorine in Medicinal Chemistry Hagmann, William K. Journal of Medicinal Chemistry, Vol. 51, Issue 15 https://doi.org/10.1021/jm800219f	journal	August 2008
Discovery of NVP-BYL719 a potent and selective phosphatidylinositol-3 kinase alpha inhibitor selected for clinical evaluation Furet, Pascal; Guagnano, Vito; Fairhurst, Robin A. Bioorganic & Medicinal Chemistry Letters, Vol. 23, Issue 13 https://doi.org/10.1016/j.bmcl.2013.05.007	journal	July 2013
Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas Zhou, Yu; Wang, Jiang; Gu, Zhanni Chemical Reviews, Vol. 116, Issue 2 https://doi.org/10.1021/acs.chemrev.5b00392	journal	January 2016
A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives McGrath, Nicholas A.; Brichacek, Matthew; Njardarson, Jon T. Journal of Chemical Education, Vol. 87, Issue 12 https://doi.org/10.1021/ed1003806	journal	December 2010
Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids Kautzky, Jacob A.; Wang, Tao; Evans, Ryan W. Journal of the American Chemical Society, Vol. 140, Issue 21 https://doi.org/10.1021/jacs.8b02650	journal	May 2018
Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids Tan, Xinqiang; Liu, Zhonglin; Shen, Haigen Journal of the American Chemical Society, Vol. 139, Issue 36 https://doi.org/10.1021/jacs.7b07944	journal	August 2017
Copper-Catalyzed Trifluoromethylation of Alkyl Bromides Kornfilt, David J. P.; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 141, Issue 17 https://doi.org/10.1021/jacs.9b03024	journal	April 2019
Metallaphotoredox Perfluoroalkylation of Organobromides Zhao, Xiangbo; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 142, Issue 46 https://doi.org/10.1021/jacs.0c09977	journal	November 2020
Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni’s Reagent Chen, Yanchi; Ma, Guobin; Gong, Hegui Organic Letters, Vol. 20, Issue 15 https://doi.org/10.1021/acs.orglett.8b02005	journal	July 2018
Interrupting the Barton–McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates Liu, Zhi-Yun; Cook, Silas P. Organic Letters, Vol. 23, Issue 3 https://doi.org/10.1021/acs.orglett.0c04039	journal	January 2021
Copper-Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Generation of a CCF₃Bond from an O-Based Electrophile Zhu, Lingui; Liu, Shasha; Douglas, Justin T. Chemistry - A European Journal, Vol. 19, Issue 38 https://doi.org/10.1002/chem.201302328	journal	August 2013
The merger of decatungstate and copper catalysis to enable aliphatic C(sp3)–H trifluoromethylation Sarver, Patrick J.; Bacauanu, Vlad; Schultz, Danielle M. Nature Chemistry, Vol. 12, Issue 5 https://doi.org/10.1038/s41557-020-0436-1	journal	March 2020
Aqueous Benzylic C–H Trifluoromethylation for Late-Stage Functionalization Guo, Shuo; AbuSalim, Deyaa I.; Cook, Silas P. Journal of the American Chemical Society, Vol. 140, Issue 39 https://doi.org/10.1021/jacs.8b08547	journal	September 2018
Copper-Catalyzed Late-Stage Benzylic C(sp3)–H Trifluoromethylation Xiao, Haiwen; Liu, Zhonglin; Shen, Haigen Chem, Vol. 5, Issue 4 https://doi.org/10.1016/j.chempr.2019.02.006	journal	April 2019
A Systematic Cheminformatics Analysis of Functional Groups Occurring in Natural Products Ertl, Peter; Schuhmann, Tim Journal of Natural Products, Vol. 82, Issue 5 https://doi.org/10.1021/acs.jnatprod.8b01022	journal	April 2019
An algorithm to identify functional groups in organic molecules Ertl, Peter Journal of Cheminformatics, Vol. 9, Issue 1 https://doi.org/10.1186/s13321-017-0225-z	journal	June 2017
Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds Henkel, Thomas; Brunne, Roger M.; Müller, Hartwig Angewandte Chemie International Edition, Vol. 38, Issue 5 https://doi.org/10.1002/(SICI)1521-3773(19990301)38:5<643::AID-ANIE643>3.0.CO;2-G	journal	March 1999
Catalytic One-Step Deoxytrifluoromethylation of Alcohols de Azambuja, Francisco; Lovrien, Sydney M.; Ross, Patrick The Journal of Organic Chemistry, Vol. 84, Issue 4 https://doi.org/10.1021/acs.joc.8b03072	journal	January 2019
Dehydroxylative Trifluoromethylthiolation, Trifluoromethylation, and Difluoromethylation of Alcohols Zhang, Wei; Lin, Jin‐Hong; Wu, Wenfeng Chinese Journal of Chemistry, Vol. 38, Issue 2 https://doi.org/10.1002/cjoc.201900364	journal	December 2019
Synthesis of trifluoromethylated compounds from alcohols via alkoxydiphenylphosphines Li, Jun-Li; Yang, Xian-Jin; Wang, Yanan Journal of Fluorine Chemistry, Vol. 178 https://doi.org/10.1016/j.jfluchem.2015.08.011	journal	October 2015
Metallaphotoredox-enabled deoxygenative arylation of alcohols Dong, Zhe; MacMillan, David W. C. Nature, Vol. 598, Issue 7881 https://doi.org/10.1038/s41586-021-03920-6	journal	August 2021
Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp³)–C(sp³) Cross-Coupling via Radical Sorting Sakai, Holt A.; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 144, Issue 14 https://doi.org/10.1021/jacs.2c02062	journal	March 2022
Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway Creutz, S. E.; Lotito, K. J.; Fu, G. C. Science, Vol. 338, Issue 6107 https://doi.org/10.1126/science.1226458	journal	November 2012
C(sp ³ )-CF ₃ Reductive Elimination from a Five-Coordinate Neutral Copper(III) Complex Liu, Shuanshuan; Liu, He; Liu, Shihan Journal of the American Chemical Society https://doi.org/10.1021/jacs.0c03304	journal	May 2020
Direct C(sp ³ )−H Trifluoromethylation of Unactivated Alkanes Enabled by Multifunctional Trifluoromethyl Copper Complexes Choi, Geunho; Lee, Geun Seok; Park, Beomsoon Angewandte Chemie International Edition, Vol. 60, Issue 10 https://doi.org/10.1002/anie.202012263	journal	January 2021
Iron-Catalyzed Photoinduced LMCT: A 1° C–H Abstraction Enables Skeletal Rearrangements and C(sp ³ )–H Alkylation Kang, Yi Cheng; Treacy, Sean M.; Rovis, Tomislav ACS Catalysis, Vol. 11, Issue 12 https://doi.org/10.1021/acscatal.1c02285	journal	June 2021
Copper Catalyzed C(sp ³ )–H Bond Alkylation via Photoinduced Ligand-to-Metal Charge Transfer Treacy, Sean M.; Rovis, Tomislav Journal of the American Chemical Society, Vol. 143, Issue 7 https://doi.org/10.1021/jacs.1c00687	journal	February 2021
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source Kariofillis, Stavros K.; Shields, Benjamin J.; Tekle-Smith, Makeda A. Journal of the American Chemical Society, Vol. 142, Issue 16 https://doi.org/10.1021/jacs.0c02805	journal	April 2020
Four-Membered Ring-Containing Spirocycles: Synthetic Strategies and Opportunities Carreira, Erick M.; Fessard, Thomas C. Chemical Reviews, Vol. 114, Issue 16 https://doi.org/10.1021/cr500127b	journal	July 2014
Metabolically Stable tert-Butyl Replacement Barnes-Seeman, David; Jain, Monish; Bell, Leslie ACS Medicinal Chemistry Letters, Vol. 4, Issue 6 https://doi.org/10.1021/ml400045j	journal	April 2013
Metabolic and Pharmaceutical Aspects of Fluorinated Compounds Johnson, Benjamin M.; Shu, Yue-Zhong; Zhuo, Xiaoliang Journal of Medicinal Chemistry, Vol. 63, Issue 12 https://doi.org/10.1021/acs.jmedchem.9b01877	journal	March 2020
Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover Phelan, James P.; Lang, Simon B.; Compton, Jordan S. Journal of the American Chemical Society, Vol. 140, Issue 25 https://doi.org/10.1021/jacs.8b05243	journal	June 2018
Ring transformation equilibrium (bond switch) in 5-(2-aminovinyl)isothiazole system via hypervalent sulfurane. Synthesis, structure determination, and kinetic study Akiba, Kinya; Kashiwagi, Kohichi; Ohyama, Yoshihiko Journal of the American Chemical Society, Vol. 107, Issue 9 https://doi.org/10.1021/ja00295a026	journal	May 1985
Generation and Alkylation of α-Carbamyl Radicals via Organic Photoredox Catalysis McManus, Joshua B.; Onuska, Nicholas P. R.; Nicewicz, David A. Journal of the American Chemical Society, Vol. 140, Issue 29 https://doi.org/10.1021/jacs.8b04890	journal	July 2018
A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation Liu, Wei; Lavagnino, Marissa N.; Gould, Colin A. Science, Vol. 374, Issue 6572 https://doi.org/10.1126/science.abl4322	journal	December 2021
Modified natural substances—fluorinated and fluoroalkylated monosaccharides and inositols Miethchen, Ralf Journal of Fluorine Chemistry, Vol. 125, Issue 6 https://doi.org/10.1016/j.jfluchem.2004.01.015	journal	June 2004
Design, properties and applications of fluorinated and fluoroalkylated N-containing monosaccharides and their analogues Bilska-Markowska, Monika; Szwajca, Anna; Marciniak, Bartosz Journal of Fluorine Chemistry, Vol. 227 https://doi.org/10.1016/j.jfluchem.2019.109364	journal	November 2019
3′-C-Trifluoromethyl Ribonucleosides Johnson, Carl R.; Bhumralkar, Dilip R.; De Clercq, Erik Nucleosides and Nucleotides, Vol. 14, Issue 1-2 https://doi.org/10.1080/15257779508014662	journal	February 1995
New Method for the Preparation of Some 2′- and 3′-Trifluoromethyl-2′,3′-dideoxyuridine Derivatives Serafinowski, Pawel J.; Brown, Catherine A. Tetrahedron, Vol. 56, Issue 2 https://doi.org/10.1016/S0040-4020(99)01007-8	journal	January 2000
Synthesis and Antiviral Evaluation of 3′-C-Trifluoromethyl Nucleoside Derivatives Bearing Adenine as the base Jeannot, Frédéric; Mathé, Christophe; Gosselin, Gilles Nucleosides, Nucleotides and Nucleic Acids, Vol. 20, Issue 4-7 https://doi.org/10.1081/NCN-100002423	journal	March 2001
Synthesis and studies of 3′-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base Jeannot, F. Bioorganic & Medicinal Chemistry, Vol. 10, Issue 10 https://doi.org/10.1016/S0968-0896(02)00216-X	journal	October 2002
Synthesis of 3′-Trifluoromethyl Nucleosides as Potential Antiviral Agents Sharma, Pawan K.; Nair, Vasu Nucleosides, Nucleotides and Nucleic Acids, Vol. 19, Issue 4 https://doi.org/10.1080/15257770008035023	journal	April 2000
Synthesis of some 2′- and 3′-Fluoroalkyl Substituted Nucleosides and Oligonucleotides Serafinowski, Pawel J.; Brown, Catherine A.; Barnes, Colin L. Nucleosides, Nucleotides and Nucleic Acids, Vol. 20, Issue 4-7 https://doi.org/10.1081/NCN-100002459	journal	March 2001

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