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Deoxytrifluoromethylation of Alcohols

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/jacs.2c04807· OSTI ID:1978492
 [1];  [2];  [2];  [2]
  1. Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States; OSTI
  2. 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, Journal Name: Journal of the American Chemical Society Journal Issue: 27 Vol. 144; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English

References (50)

Discovery of NVP-BYL719 a potent and selective phosphatidylinositol-3 kinase alpha inhibitor selected for clinical evaluation journal July 2013
Metabolically Stable tert-Butyl Replacement journal April 2013
New Method for the Preparation of Some 2′- and 3′-Trifluoromethyl-2′,3′-dideoxyuridine Derivatives journal January 2000
The merger of decatungstate and copper catalysis to enable aliphatic C(sp3)–H trifluoromethylation journal March 2020
Iron-Catalyzed Photoinduced LMCT: A 1° C–H Abstraction Enables Skeletal Rearrangements and C(sp 3 )–H Alkylation journal June 2021
Modified natural substances—fluorinated and fluoroalkylated monosaccharides and inositols journal June 2004
What is in Our Kit? An Analysis of Building Blocks Used in Medicinal Chemistry Parallel Libraries journal November 2021
Catalytic One-Step Deoxytrifluoromethylation of Alcohols journal January 2019
3′-C-Trifluoromethyl Ribonucleosides journal February 1995
A Systematic Cheminformatics Analysis of Functional Groups Occurring in Natural Products journal April 2019
An algorithm to identify functional groups in organic molecules journal June 2017
Aqueous Benzylic C–H Trifluoromethylation for Late-Stage Functionalization journal September 2018
Metallaphotoredox-enabled deoxygenative arylation of alcohols journal August 2021
Metallaphotoredox Perfluoroalkylation of Organobromides journal November 2020
C(sp 3 )-CF 3 Reductive Elimination from a Five-Coordinate Neutral Copper(III) Complex journal May 2020
Dehydroxylative Trifluoromethylthiolation, Trifluoromethylation, and Difluoromethylation of Alcohols journal December 2019
Synthesis of 3′-Trifluoromethyl Nucleosides as Potential Antiviral Agents journal April 2000
The Many Roles for Fluorine in Medicinal Chemistry journal August 2008
Four-Membered Ring-Containing Spirocycles: Synthetic Strategies and Opportunities journal July 2014
Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover journal June 2018
Copper-Catalyzed Trifluoromethylation of Alkyl Bromides journal April 2019
Copper-Catalyzed Late-Stage Benzylic C(sp3)–H Trifluoromethylation journal April 2019
A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives journal December 2010
Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni’s Reagent journal July 2018
Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway journal November 2012
Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas journal January 2016
Synthesis and Antiviral Evaluation of 3′-C-Trifluoromethyl Nucleoside Derivatives Bearing Adenine as the base journal March 2001
Metabolic and Pharmaceutical Aspects of Fluorinated Compounds journal March 2020
Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds journal March 1999
Copper Catalyzed C(sp 3 )–H Bond Alkylation via Photoinduced Ligand-to-Metal Charge Transfer journal February 2021
Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids journal August 2017
Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?: Miniperspective journal December 2015
Interrupting the Barton–McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates journal January 2021
Copper-Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Generation of a CCF3Bond from an O-Based Electrophile journal August 2013
Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp 2 )–C(sp 3 ) Cross-Coupling Methods by Library Synthesis journal March 2020
Direct C(sp 3 )−H Trifluoromethylation of Unactivated Alkanes Enabled by Multifunctional Trifluoromethyl Copper Complexes journal January 2021
Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids journal May 2018
Synthesis of trifluoromethylated compounds from alcohols via alkoxydiphenylphosphines journal October 2015
A biomimetic S H 2 cross-coupling mechanism for quaternary sp 3 -carbon formation journal December 2021
Generation and Alkylation of α-Carbamyl Radicals via Organic Photoredox Catalysis journal July 2018
Ring transformation equilibrium (bond switch) in 5-(2-aminovinyl)isothiazole system via hypervalent sulfurane. Synthesis, structure determination, and kinetic study journal May 1985
Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design journal February 2018
Organic synthesis provides opportunities to transform drug discovery journal March 2018
Synthesis and studies of 3′-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base journal October 2002
Design, properties and applications of fluorinated and fluoroalkylated N-containing monosaccharides and their analogues journal November 2019
Synthesis of some 2′- and 3′-Fluoroalkyl Substituted Nucleosides and Oligonucleotides journal March 2001
What Do Medicinal Chemists Actually Make? A 50-Year Retrospective journal August 2011
Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success journal November 2009
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source journal April 2020
Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp3)–C(sp3) Cross-Coupling via Radical Sorting journal March 2022

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