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Literature DB >> 25294948

Copper-Catalyzed Decarboxylative Trifluoromethylation of Propargyl Bromodifluoroacetates.

Brett R Ambler¹, Santosh Peddi², Ryan A Altman¹.

Abstract

The development of efficient methods for accessing fluorinated functional groups is desirable. Herein, we report a two-step method that utilizes catalytic Cu for the decarboxylative trifluoromethylation of propargyl bromodifluoroacetates. This protocol affords a mixture of propargyl trifluoromethanes and trifluoromethyl allenes.

Entities: Chemical Disease Gene

Keywords: alkynes; catalysis; copper; decarboxylation; trifluoromethylation

Year: 2014 PMID： 25294948 PMCID： PMC4185158 DOI： 10.1055/s-0033-1339128

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

22 in total

1. Introduction of fluorine and fluorine-containing functional groups.

Authors: Theresa Liang; Constanze N Neumann; Tobias Ritter
Journal: Angew Chem Int Ed Engl Date: 2013-07-19 Impact factor: 15.336

Review 2. A "Renaissance" in radical trifluoromethylation.

Authors: Armido Studer
Journal: Angew Chem Int Ed Engl Date: 2012-08-13 Impact factor: 15.336

3. Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates.

Authors: Brett R Ambler; Ryan A Altman
Journal: Org Lett Date: 2013-10-11 Impact factor: 6.005

4. A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides.

Authors: Hiroyuki Morimoto; Tetsu Tsubogo; Nichole D Litvinas; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2011-03-25 Impact factor: 15.336

5. Cu-mediated chemoselective trifluoromethylation of benzyl bromides using shelf-stable electrophilic trifluoromethylating reagents.

Authors: Hiroyuki Kawai; Tatsuya Furukawa; Yoshinori Nomura; Etsuko Tokunaga; Norio Shibata
Journal: Org Lett Date: 2011-06-13 Impact factor: 6.005

6. Copper-catalyzed trifluoromethylation of terminal alkenes through allylic C-H bond activation.

Authors: Jun Xu; Yao Fu; Dong-Fen Luo; Yuan-Ye Jiang; Bin Xiao; Zhao-Jing Liu; Tian-Jun Gong; Lei Liu
Journal: J Am Chem Soc Date: 2011-09-13 Impact factor: 15.419

7. Direct cupration of fluoroform.

Authors: Alessandro Zanardi; Maxim A Novikov; Eddy Martin; Jordi Benet-Buchholz; Vladimir V Grushin
Journal: J Am Chem Soc Date: 2011-12-02 Impact factor: 15.419

8. Trifluoromethylation of aryl and heteroaryl halides with fluoroform-derived CuCF3: scope, limitations, and mechanistic features.

Authors: Anton Lishchynskyi; Maxim A Novikov; Eddy Martin; Eduardo C Escudero-Adán; Petr Novák; Vladimir V Grushin
Journal: J Org Chem Date: 2013-08-21 Impact factor: 4.354

9. Active trifluoromethylating agents from well-defined Copper(I)-CF3 complexes.

Authors: Galyna G Dubinina; Hideki Furutachi; David A Vicic
Journal: J Am Chem Soc Date: 2008-06-11 Impact factor: 15.419

10. Ruthenium catalyzed reductive coupling of paraformaldehyde to trifluoromethyl allenes: CF3-bearing all-carbon quaternary centers.

Authors: Brannon Sam; T Patrick Montgomery; Michael J Krische
Journal: Org Lett Date: 2013-07-10 Impact factor: 6.005

5 in total

5. Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols.

Authors: Daniels Posevins; Aitor Bermejo-López; Jan-E Bäckvall
Journal: Angew Chem Int Ed Engl Date: 2021-09-02 Impact factor: 16.823