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Literature DB >> 24138611

An improved catalyst system for the Pd-catalyzed fluorination of (hetero)aryl triflates.

Hong Geun Lee¹, Phillip J Milner¹, Stephen L Buchwald¹.

Abstract

The stable Pd(0) species [(1,5-cyclooctadiene)(L·Pd)2] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.

Entities: Chemical Gene

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Year: 2013 PMID： 24138611 PMCID： PMC3858322 DOI： 10.1021/ol402859k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

34 in total

1. 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

Review 2. Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

Authors: Philip W Miller; Nicholas J Long; Ramon Vilar; Antony D Gee
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

Authors: Kelvin S L Chan; Masayuki Wasa; Xisheng Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2011-07-11 Impact factor: 15.336

An improved catalyst system for the Pd-catalyzed fluorination of (hetero)aryl triflates.

1. Palladium-mediated fluorination of arylboronic acids.

Review 2. Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

3. Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

4. Deoxyfluorination of phenols.

5. Silver-catalyzed late-stage fluorination.

6. Copper-mediated fluorination of arylboronate esters. Identification of a copper(III) fluoride complex.

Review 7. The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

8. Capsaicin, a component of red peppers, inhibits the growth of androgen-independent, p53 mutant prostate cancer cells.

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

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

1. Organic chemistry: A cure for catalyst poisoning.

2. Application of a robustness screen for the evaluation of synthetic organic methodology.

3. Structure and Reactivity of [(L•Pd)_n•(1,5-cyclooctadiene)] (n=1-2) Complexes Bearing Biaryl Phosphine Ligands.

4. Well-defined nickel and palladium precatalysts for cross-coupling.

5. Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

6. Unexpected Formation of Hexasubstituted Arenes through a 2-fold Palladium-Mediated Ligand Arylation.

7. Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF₃ as an Additive.

8. Off-Cycle Processes in Pd-Catalyzed Cross-Coupling of Carboranes.

9. Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

10. Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.