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Literature DB >> 21235259

Room temperature aryl trifluoromethylation via copper-mediated oxidative cross-coupling.

Todd D Senecal¹, Andrew T Parsons, Stephen L Buchwald.

Abstract

A method for the room temperature copper-mediated trifluoromethylation of aryl and heteroaryl boronic acids has been developed. This protocol is amenable to normal benchtop setup and reactions typically require only 1-4 h. Proceeding under mild conditions, the method tolerates a range of functional groups, allowing access to a variety of trifluoromethylarenes.

Entities: Chemical Gene

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Year: 2011 PMID： 21235259 PMCID： PMC3093444 DOI： 10.1021/jo1023377

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

13 in total

1. Perfluoroalkylation with Organosilicon Reagents.

Authors: G. K. Surya Prakash; Andrei K. Yudin
Journal: Chem Rev Date: 1997-05-08 Impact factor: 60.622

2. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors: Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal: Chem Rev Date: 2002-05 Impact factor: 60.622

3. Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with Me3SiCF3.

Authors: Lingling Chu; Feng-Ling Qing
Journal: J Am Chem Soc Date: 2010-06-02 Impact factor: 15.419

4. Copper-mediated oxidative trifluoromethylation of boronic acids.

Authors: Lingling Chu; Feng-Ling Qing
Journal: Org Lett Date: 2010-11-05 Impact factor: 6.005

5. Facile Ar-CF3 bond formation at Pd. Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph].

Authors: Vladimir V Grushin; William J Marshall
Journal: J Am Chem Soc Date: 2006-10-04 Impact factor: 15.419

6. The palladium-catalyzed trifluoromethylation of aryl chlorides.

Authors: Eun Jin Cho; Todd D Senecal; Tom Kinzel; Yong Zhang; Donald A Watson; Stephen L Buchwald
Journal: Science Date: 2010-06-25 Impact factor: 47.728

7. Pd(II)-catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter.

Authors: Xisheng Wang; Larry Truesdale; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

8. A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors: Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

9. Aryl-CF(3) bond-forming reductive elimination from palladium(IV).

Authors: Nicholas D Ball; Jeff W Kampf; Melanie S Sanford
Journal: J Am Chem Soc Date: 2010-03-10 Impact factor: 15.419

10. 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

26 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

Room temperature aryl trifluoromethylation via copper-mediated oxidative cross-coupling.

1. Perfluoroalkylation with Organosilicon Reagents.

2. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

3. Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with Me3SiCF3.

4. Copper-mediated oxidative trifluoromethylation of boronic acids.

5. Facile Ar-CF3 bond formation at Pd. Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph].

6. The palladium-catalyzed trifluoromethylation of aryl chlorides.

7. Pd(II)-catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter.

8. A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

9. Aryl-CF(3) bond-forming reductive elimination from palladium(IV).

10. 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. Investigations into Transition Metal Catalyzed Arene Trifluoromethylation Reactions.

5. Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Review 6. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

7. Metallaphotoredox Perfluoroalkylation of Organobromides.

Review 8. Catalysis for fluorination and trifluoromethylation.

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

10. The palladium-catalyzed trifluoromethylation of vinyl sulfonates.