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Literature DB >> 24123499

Directing-group-assisted copper-catalyzed olefinic trifluoromethylation of electron-deficient alkenes.

Abstract

Assistance provided: The directing group in the title reaction not only activates the substrates but also allows the stereospecific formation of cis-trifluoromethylated products. The reaction is operationally simple and tolerates a wide variety of functional groups, thus providing an efficient method for the stereoselective synthesis of β-CF3 -functionalized acrylamide derivatives.

Entities: Chemical

Keywords: CH activation; alkenes; copper; cross-coupling; trifluoromethylation

Mesh：

Substances：

Year: 2013 PMID： 24123499 DOI： 10.1002/anie.201307245

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

9 in total

1. 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

Review 2. Recent advances in direct trifluoromethylation of olefinic C-H bonds.

Authors: Cao Yang; Akbar Hassanpour; Khatereh Ghorbanpour; Shahrzad Abdolmohammadi; Esmail Vessally
Journal: RSC Adv Date: 2019-09-03 Impact factor: 4.036

3. Rhodium-catalysed C(sp(2))-C(sp(2)) bond formation via C-H/C-F activation.

Authors: Panpan Tian; Chao Feng; Teck-Peng Loh
Journal: Nat Commun Date: 2015-06-17 Impact factor: 14.919

4. Product Control in Alkene Trifluoromethylation: Hydrotrifluoromethylation, Vinylic Trifluoromethylation, and Iodotrifluoromethylation using Togni Reagent.

Authors: Hiromichi Egami; Yoshihiko Usui; Shintaro Kawamura; Sayoko Nagashima; Mikiko Sodeoka
Journal: Chem Asian J Date: 2015-06-16

Directing-group-assisted copper-catalyzed olefinic trifluoromethylation of electron-deficient alkenes.

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

Review 2. Recent advances in direct trifluoromethylation of olefinic C-H bonds.

3. Rhodium-catalysed C(sp(2))-C(sp(2)) bond formation via C-H/C-F activation.

4. Product Control in Alkene Trifluoromethylation: Hydrotrifluoromethylation, Vinylic Trifluoromethylation, and Iodotrifluoromethylation using Togni Reagent.

5. The dual role of thiourea in the thiotrifluoromethylation of alkenes.

6. Copper-catalyzed remote C(sp³)-H azidation and oxidative trifluoromethylation of benzohydrazides.

Review 7. Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

8. Geminal group-directed olefinic C-H functionalization via four- to eight-membered exo-metallocycles.

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