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Literature DB >> 20155920

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

Nicholas D Ball¹, Jeff W Kampf, Melanie S Sanford.

Abstract

This communication describes oxidatively induced Ar-CF(3) bond-forming reductive elimination from new Pd(II) complexes of general structure (L approximately L)Pd(II)(Ar)(CF(3)). The electrophilic fluorinating reagent N-fluoro-2,4,6-trimethylpyridinium triflate promotes these reactions in good to excellent yields. The palladium(IV) intermediate ((t)Bu-bpy)Pd(IV)(CF(3))(F)(OTf)(C(6)H(4)F) has been isolated, characterized, and demonstrated to undergo high yielding Ar-CF(3) coupling upon thermolysis. This work provides an attractive conceptual framework for the development of Pd(II/IV)-catalyzed arene trifluoromethylation reactions.

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Year: 2010 PMID： 20155920 PMCID： PMC2832076 DOI： 10.1021/ja100955x

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

21 in total

Review 1. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors: Jun-An Ma; Dominique Cahard
Journal: Chem Rev Date: 2004-12 Impact factor: 60.622

2. 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

3. Palladium-mediated fluorination of arylboronic acids.

Authors: Takeru Furuya; Hanns Martin Kaiser; Tobias Ritter
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. 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

Review 5. The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

Authors: Vladimir V Grushin
Journal: Acc Chem Res Date: 2010-01-19 Impact factor: 22.384

6. High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

Authors: Kilian Muñiz
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7. 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

8. Versatile Pd(OTf)2 x 2 H2O-catalyzed ortho-fluorination using NMP as a promoter.

Authors: Xisheng Wang; Tian-Sheng Mei; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2009-06-10 Impact factor: 15.419

9. Synthesis and reactivity of a mono-sigma-aryl palladium(IV) fluoride complex.

Authors: Nicholas D Ball; Melanie S Sanford
Journal: J Am Chem Soc Date: 2009-03-25 Impact factor: 15.419

10. Xenon difluoride induced aryl iodide reductive elimination: a simple access to difluoropalladium(II) complexes.

Authors: Ariela W Kaspi; Anette Yahav-Levi; Israel Goldberg; Arkadi Vigalok
Journal: Inorg Chem Date: 2007-12-04 Impact factor: 5.165

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

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

Review 1. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

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

3. Palladium-mediated fluorination of arylboronic acids.

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

Review 5. The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

6. High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

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

8. Versatile Pd(OTf)2 x 2 H2O-catalyzed ortho-fluorination using NMP as a promoter.

9. Synthesis and reactivity of a mono-sigma-aryl palladium(IV) fluoride complex.

10. Xenon difluoride induced aryl iodide reductive elimination: a simple access to difluoropalladium(II) 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. C-H bond activation at palladium(IV) centers.

Review 7. Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry.

Review 8. Catalysis for fluorination and trifluoromethylation.

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

10. Pd-catalyzed C-H fluorination with nucleophilic fluoride.