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Literature DB >> 19249867

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

Abstract

This communication describes the rational design and synthesis of the remarkably stable Pd(IV) monoaryl fluoride complex (t-Bu-bpy)Pd(IV)(p-FC(6)H(4))(F)(2)(FHF) (t-Bu-bpy = 4,4'-di-tert-butyl-2,2'-bipyridine). This and related complexes undergo Ar-F bond formation in the presence of "F(+)" sources. This work serves as a foundation for the development of Pd(II/IV)-catalyzed coupling reactions to form aryl fluorides.

Entities: Chemical Disease Gene Species

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Year: 2009 PMID： 19249867 PMCID： PMC2713824 DOI： 10.1021/ja8054595

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

16 in total

1. Reductive elimination of aryl halides from palladium(II).

Authors: A H Roy; J F Hartwig
Journal: J Am Chem Soc Date: 2001-02-14 Impact factor: 15.419

2. Unusually stable palladium(IV) complexes: detailed mechanistic investigation of C-O bond-forming reductive elimination.

Authors: Allison R Dick; Jeff W Kampf; Melanie S Sanford
Journal: J Am Chem Soc Date: 2005-09-21 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. Anhydrous tetrabutylammonium fluoride.

Authors: Haoran Sun; Stephen G DiMagno
Journal: J Am Chem Soc Date: 2005-02-23 Impact factor: 15.419

5. Palladium-catalyzed fluorination of carbon-hydrogen bonds.

Authors: Kami L Hull; Waseem Q Anani; Melanie S Sanford
Journal: J Am Chem Soc Date: 2006-06-07 Impact factor: 15.419

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. Aryl-fluoride reductive elimination from Pd(II): feasibility assessment from theory and experiment.

Authors: Dmitry V Yandulov; Ngon T Tran
Journal: J Am Chem Soc Date: 2007-02-07 Impact factor: 15.419

8. Metal-mediated formation of carbon-halogen bonds.

Authors: Arkadi Vigalok
Journal: Chemistry Date: 2008 Impact factor: 5.236

9. trans-Difluoro complexes of palladium(II).

Authors: Vladimir V Grushin; William J Marshall
Journal: J Am Chem Soc Date: 2009-01-28 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

45 in total

1. 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

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

1. Reductive elimination of aryl halides from palladium(II).

2. Unusually stable palladium(IV) complexes: detailed mechanistic investigation of C-O bond-forming reductive elimination.

3. Palladium-mediated fluorination of arylboronic acids.

4. Anhydrous tetrabutylammonium fluoride.

5. Palladium-catalyzed fluorination of carbon-hydrogen bonds.

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

7. Aryl-fluoride reductive elimination from Pd(II): feasibility assessment from theory and experiment.

8. Metal-mediated formation of carbon-halogen bonds.

9. trans-Difluoro complexes of palladium(II).

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

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

2. Radiochemistry: Flipping fluoride's reactivity.

3. Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.

4. Accelerating palladium-catalyzed C-F bond formation: use of a microflow packed-bed reactor.

5. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

6. Investigations into Transition Metal Catalyzed Arene Trifluoromethylation Reactions.

7. Deoxyfluorination of phenols.

Review 8. Catalysis for fluorination and trifluoromethylation.

9. Steric Crowding Makes Challenging C(sp3)-F Reductive Eliminations Feasible.

10. Catalytic enantioselective cyclization and C3-fluorination of polyenes.