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Literature DB >> 23373772

Catalytic hydrotrifluoromethylation of unactivated alkenes.

Satoshi Mizuta¹, Stefan Verhoog, Keary M Engle, Tanatorn Khotavivattana, Miriam O'Duill, Katherine Wheelhouse, Gerasimos Rassias, Maurice Médebielle, Véronique Gouverneur.

Abstract

A visible-light-mediated hydrotrifluoromethylation of unactivated alkenes that uses the Umemoto reagent as the CF(3) source and MeOH as the reductant is disclosed. This effective transformation operates at room temperature in the presence of 5 mol % Ru(bpy)(3)Cl(2); the process is characterized by its operational simplicity and functional group tolerance.

Entities: Chemical

Mesh：

Substances：
Alkenes
Fluorine

Year: 2013 PMID： 23373772 DOI： 10.1021/ja401022x

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

Keyword Cloud
Cited

20 in total

1. Synthesis and applications of α-trifluoromethylated alkylboron compounds.

Authors: O Andreea Argintaru; DaWeon Ryu; Ioana Aron; Gary A Molander
Journal: Angew Chem Int Ed Engl Date: 2013-11-07 Impact factor: 15.336

Review 2. Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications.

Authors: Xiaoran Roger Liu; Mengru Mira Zhang; Michael L Gross
Journal: Chem Rev Date: 2020-04-22 Impact factor: 60.622

3. Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

Authors: Joel W Beatty; James J Douglas; Richard Miller; Rory C McAtee; Kevin P Cole; Corey R J Stephenson
Journal: Chem Date: 2016-09-08 Impact factor: 22.804

4. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors: Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal: Chem Rev Date: 2019-06-25 Impact factor: 60.622

5. Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF₃⁺, CF₃^•, and CF₃^- Reactivity.

Authors: Hao Jia; Andreas P Häring; Florian Berger; Li Zhang; Tobias Ritter
Journal: J Am Chem Soc Date: 2021-05-14 Impact factor: 15.419

6. Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Authors: Yong Li; Zhishi Ye; Tabitha M Bellman; Teng Chi; Mingji Dai
Journal: Org Lett Date: 2015-04-17 Impact factor: 6.072

Catalytic hydrotrifluoromethylation of unactivated alkenes.

1. Synthesis and applications of α-trifluoromethylated alkylboron compounds.

Review 2. Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications.

3. Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

4. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

5. Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF₃⁺, CF₃^•, and CF₃^- Reactivity.

6. Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Review 7. Addition of CF3 across unsaturated moieties: a powerful functionalization tool.

Review 8. Radiosynthesis of [18)F]trifluoroalkyl groups: scope and limitations.

9. Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent.

10. Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis.