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 Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.

Literature DB >> 23687958

Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.

Satoshi Mizuta¹, Ida S R Stenhagen, Miriam O'Duill, Jamie Wolstenhulme, Anna K Kirjavainen, Sarita J Forsback, Matthew Tredwell, Graham Sandford, Peter R Moore, Mickael Huiban, Sajinder K Luthra, Jan Passchier, Olof Solin, Véronique Gouverneur.

Abstract

Treatment of readily available α,α-difluoro- and α-fluoroarylacetic acids with Selectfluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [(18)F]labeling is demonstrated using [(18)F]Selectfluor bis(triflate), a reagent affording [(18)F]tri- and [(18)F]difluoromethylarenes not within reach with [(18)F]F2.

Entities: Chemical

Mesh：

Substances：

Year: 2013 PMID： 23687958 DOI： 10.1021/ol4009377

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

Keyword Cloud
Cited

19 in total

1. Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters.

Authors: Edward Miller; Suhong Kim; Katarina Gibson; Jeffrey S Derrick; F Dean Toste
Journal: J Am Chem Soc Date: 2020-04-30 Impact factor: 15.419

2. Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

Authors: Hang Shi; Augustin Braun; Lu Wang; Steven H Liang; Neil Vasdev; Tobias Ritter
Journal: Angew Chem Int Ed Engl Date: 2016-08-05 Impact factor: 15.336

3. A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging.

Authors: Mickael Huiban; Matthew Tredwell; Satoshi Mizuta; Zehong Wan; Xiaomin Zhang; Thomas Lee Collier; Véronique Gouverneur; Jan Passchier
Journal: Nat Chem Date: 2013-09-08 Impact factor: 24.427

Review 4. Decarboxylative fluorination strategies for accessing medicinally- relevant products.

Authors: Yupu Qiao; Lingui Zhu; Brett R Ambler; Ryan A Altman
Journal: Curr Top Med Chem Date: 2014 Impact factor: 3.295

5. Metal-free ¹⁸F-labeling of aryl-CF₂H via nucleophilic radiofluorination and oxidative C-H activation.

Authors: Gengyang Yuan; Feng Wang; Nickeisha A Stephenson; Lu Wang; Benjamin H Rotstein; Neil Vasdev; Pingping Tang; Steven H Liang
Journal: Chem Commun (Camb) Date: 2016-12-20 Impact factor: 6.222

6. [¹⁸F]Difluorocarbene for positron emission tomography.

Authors: Jeroen B I Sap; Claudio F Meyer; Joseph Ford; Natan J W Straathof; Alexander B Dürr; Mariah J Lelos; Stephen J Paisey; Tim A Mollner; Sandrine M Hell; Andrés A Trabanco; Christophe Genicot; Christopher W Am Ende; Robert S Paton; Matthew Tredwell; Véronique Gouverneur
Journal: Nature Date: 2022-03-28 Impact factor: 69.504

Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.

1. Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters.

2. Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

3. A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging.

Review 4. Decarboxylative fluorination strategies for accessing medicinally- relevant products.

5. Metal-free ¹⁸F-labeling of aryl-CF₂H via nucleophilic radiofluorination and oxidative C-H activation.

6. [¹⁸F]Difluorocarbene for positron emission tomography.

7. Decarboxylative Halogenation of Organic Compounds.

8. Mechanism of Electrophilic Fluorination with Pd(IV): Fluoride Capture and Subsequent Oxidative Fluoride Transfer^.

9. Difluoroalkylation of Tertiary Amides and Lactams by an Iridium-Catalyzed Reductive Reformatsky Reaction.

10. Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent.