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Literature DB >> 22624669

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

Abstract

This communication describes the development of a mild method for the cross-coupling of arylboronic acids with CF(3)I via the merger of photoredox and Cu catalysis. This method has been applied to the trifluoromethylation of electronically diverse aromatic and heteroaromatic substrates and tolerates many common functional groups.

Entities: CellLine Chemical

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Year: 2012 PMID： 22624669 PMCID： PMC3415565 DOI： 10.1021/ja301553c

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

42 in total

1. 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

2. Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes.

Authors: Lingling Chu; Feng-Ling Qing
Journal: J Am Chem Soc Date: 2011-12-21 Impact factor: 15.419

3. 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

4. Photoredox catalysis: a mild, operationally simple approach to the synthesis of α-trifluoromethyl carbonyl compounds.

Authors: Phong V Pham; David A Nagib; David W C MacMillan
Journal: Angew Chem Int Ed Engl Date: 2011-05-23 Impact factor: 15.336

5. A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen)CuR(F)].

Authors: Nichole D Litvinas; Patrick S Fier; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2011-11-14 Impact factor: 15.336

6. Unexpected H2O-induced Ar-X activation with trifluoromethylpalladium(II) aryls.

Authors: Vladimir V Grushin; William J Marshall
Journal: J Am Chem Soc Date: 2006-04-12 Impact factor: 15.419

7. Experimental and theoretical studies on radical trifluoromethylation of titanium ate and lithium enolates.

Authors: Yoshimitsu Itoh; K N Houk; Koichi Mikami
Journal: J Org Chem Date: 2006-11-10 Impact factor: 4.354

8. Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent.

Authors: Tianfei Liu; Qilong Shen
Journal: Org Lett Date: 2011-04-07 Impact factor: 6.005

Review 9. CF(3)-bearing aromatic and heterocyclic building blocks.

Authors: Manfred Schlosser
Journal: Angew Chem Int Ed Engl Date: 2006-08-18 Impact factor: 15.336

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

68 in total

1. Investigations into Transition Metal Catalyzed Arene Trifluoromethylation Reactions.

Authors: Yingda Ye; Melanie S Sanford
Journal: Synlett Date: 2012-09-01 Impact factor: 2.454

2. Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.

Authors: Sharon R Neufeldt; Melanie S Sanford
Journal: Adv Synth Catal Date: 2012-12-14 Impact factor: 5.837

10. Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

Authors: Giulia Bergonzini; Corinna S Schindler; Carl-Johan Wallentin; Eric N Jacobsen; Corey R J Stephenson
Journal: Chem Sci Date: 2014-01 Impact factor: 9.825

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

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

2. Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes.

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

4. Photoredox catalysis: a mild, operationally simple approach to the synthesis of α-trifluoromethyl carbonyl compounds.

5. A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen)CuR(F)].

6. Unexpected H2O-induced Ar-X activation with trifluoromethylpalladium(II) aryls.

7. Experimental and theoretical studies on radical trifluoromethylation of titanium ate and lithium enolates.

8. Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent.

Review 9. CF(3)-bearing aromatic and heterocyclic building blocks.

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

1. Investigations into Transition Metal Catalyzed Arene Trifluoromethylation Reactions.

2. Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.

3. Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

4. Preparation of visible-light-activated metal complexes and their use in photoredox/nickel dual catalysis.

5. Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light.

6. Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Review 7. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

8. Transition metal photoredox catalysis of radical thiol-ene reactions.

9. Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.

10. Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.