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Literature DB >> 18543912

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

Galyna G Dubinina¹, Hideki Furutachi, David A Vicic.

Abstract

The first examples of isolable and structurally characterized Cu(I)-CF3 complexes are reported. N-Heterocyclic carbene (NHC)-supported copper tert-butoxide complexes reacted with Me3Si-CF3 to afford new (NHC)Cu-CF3 complexes whose structures were dependent on whether or not the C4-C5 positions of the five-membered NHC rings were saturated. In situ generated (SIiPr)Cu-CF3 cleanly transferred its trifluoromethyl group to a number of organic halides under mild conditions.

Entities: Chemical Disease

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Year: 2008 PMID： 18543912 DOI： 10.1021/ja802946s

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

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Cited

32 in total

1. Silver-mediated trifluoromethylation of arenes using TMSCF3.

Authors: Yingda Ye; Shin Hee Lee; Melanie S Sanford
Journal: Org Lett Date: 2011-09-20 Impact factor: 6.005

2. Mechanistic and computational studies of oxidatively-induced aryl-CF3 bond-formation at Pd: rational design of room temperature aryl trifluoromethylation.

Authors: Nicholas D Ball; J Brannon Gary; Yingda Ye; Melanie S Sanford
Journal: J Am Chem Soc Date: 2011-04-22 Impact factor: 15.419

3. Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I.

Authors: Yingda Ye; Melanie S Sanford
Journal: J Am Chem Soc Date: 2012-05-24 Impact factor: 15.419

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

1. Silver-mediated trifluoromethylation of arenes using TMSCF3.

2. Mechanistic and computational studies of oxidatively-induced aryl-CF3 bond-formation at Pd: rational design of room temperature aryl trifluoromethylation.

3. Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I.

4. Catalysis: Fluorination made easier.

5. Investigations into Transition Metal Catalyzed Arene Trifluoromethylation Reactions.

6. Metallaphotoredox Perfluoroalkylation of Organobromides.

7. Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

Review 8. Catalysis for fluorination and trifluoromethylation.

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

10. Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.