Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Copper-mediated fluorination of aryl iodides.

Literature DB >> 22709145

Copper-mediated fluorination of aryl iodides.

Abstract

The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper(III) fluoride.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2012 PMID： 22709145 PMCID： PMC3487470 DOI： 10.1021/ja304410x

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

14 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

2. Deoxyfluorination of phenols.

Authors: Pingping Tang; Weike Wang; Tobias Ritter
Journal: J Am Chem Soc Date: 2011-07-12 Impact factor: 15.419

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

Authors: Hiroyuki Morimoto; Tetsu Tsubogo; Nichole D Litvinas; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2011-03-25 Impact factor: 15.336

4. 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

5. Silver-mediated fluorination of aryl silanes.

Authors: Pingping Tang; Tobias Ritter
Journal: Tetrahedron Date: 2011-06-17 Impact factor: 2.457

6. Silver-catalyzed late-stage fluorination.

Authors: Pingping Tang; Takeru Furuya; Tobias Ritter
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

Review 7. 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

8. Fluorination of boronic acids mediated by silver(I) triflate.

Authors: Takeru Furuya; Tobias Ritter
Journal: Org Lett Date: 2009-07-02 Impact factor: 6.005

9. Synthesis and reactivity of functionalized arylcopper compounds by transmetalation of organosilanes.

Authors: Jessica R Herron; Zachary T Ball
Journal: J Am Chem Soc Date: 2008-12-10 Impact factor: 15.419

10. Silver-mediated fluorination of functionalized aryl stannanes.

Authors: Takeru Furuya; Alexandra E Strom; Tobias Ritter
Journal: J Am Chem Soc Date: 2009-02-11 Impact factor: 15.419

34 in total

1. Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Authors: Ruth Dorel; Philip Boehm; Daniel P Schwinger; John F Hartwig
Journal: Chemistry Date: 2020-01-28 Impact factor: 5.236

Review 2. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Authors: Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal: Chem Rev Date: 2019-01-30 Impact factor: 60.622

Copper-mediated fluorination of aryl iodides.

1. Palladium-mediated fluorination of arylboronic acids.

2. Deoxyfluorination of phenols.

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

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

5. Silver-mediated fluorination of aryl silanes.

6. Silver-catalyzed late-stage fluorination.

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

8. Fluorination of boronic acids mediated by silver(I) triflate.

9. Synthesis and reactivity of functionalized arylcopper compounds by transmetalation of organosilanes.

10. Silver-mediated fluorination of functionalized aryl stannanes.

1. Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Review 2. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Review 3. Fluorine-18 patents (2009-2015). Part 2: new radiochemistry.

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

5. C-H ¹⁸F-fluorination of 8-methylquinolines with Ag[¹⁸F]F.

6. NHC-Copper Mediated Ligand-Directed Radiofluorination of Aryl Halides.

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

8. Palladium(III)-catalyzed fluorination of arylboronic acid derivatives.

9. Nickel-mediated oxidative fluorination for PET with aqueous [18F] fluoride.

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

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

Review 2. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Review 3. Fluorine-18 patents (2009-2015). Part 2: new radiochemistry.

Review 2. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.