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Literature DB >> 25881929

Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

Sandrine Ventre¹, Filip R Petronijevic¹, David W C MacMillan¹.

Abstract

The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F(•) transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

Entities: Chemical Disease Gene

Mesh：

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Year: 2015 PMID： 25881929 PMCID： PMC4862610 DOI： 10.1021/jacs.5b02244

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

33 in total

1. Visible light photoredox catalysis: applications in organic synthesis.

Authors: Jagan M R Narayanam; Corey R J Stephenson
Journal: Chem Soc Rev Date: 2010-06-08 Impact factor: 54.564

Review 2. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

3. Direct C-F bond formation using photoredox catalysis.

Authors: Montserrat Rueda-Becerril; Olivier Mahé; Myriam Drouin; Marek B Majewski; Julian G West; Michael O Wolf; Glenn M Sammis; Jean-François Paquin
Journal: J Am Chem Soc Date: 2014-01-30 Impact factor: 15.419

4. Enantioselective organocatalytic alpha-fluorination of aldehydes.

Authors: Teresa D Beeson; David W C Macmillan
Journal: J Am Chem Soc Date: 2005-06-22 Impact factor: 15.419

5. Palladium-catalyzed regio- and enantioselective fluorination of acyclic allylic halides.

Authors: Matthew H Katcher; Allen Sha; Abigail G Doyle
Journal: J Am Chem Soc Date: 2011-09-19 Impact factor: 15.419

Review 6. Solar synthesis: prospects in visible light photocatalysis.

Authors: Danielle M Schultz; Tehshik P Yoon
Journal: Science Date: 2014-02-28 Impact factor: 47.728

Review 7. Carbon-fluorine bond formation.

Authors: Takeru Furuya; Christian A Kuttruff; Tobias Ritter
Journal: Curr Opin Drug Discov Devel Date: 2008-11

8. Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore.

Authors: Zhiwei Zuo; David W C MacMillan
Journal: J Am Chem Soc Date: 2014-03-31 Impact factor: 15.419

9. Pd-catalyzed nucleophilic fluorination of aryl bromides.

Authors: Hong Geun Lee; Phillip J Milner; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2014-02-27 Impact factor: 15.419

10. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

Authors: Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W C MacMillan
Journal: J Am Chem Soc Date: 2014-07-28 Impact factor: 15.419

34 in total

1. Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors: Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal: Org Lett Date: 2018-11-08 Impact factor: 6.005

2. Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors: Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal: J Am Chem Soc Date: 2015-08-28 Impact factor: 15.419

Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

1. Visible light photoredox catalysis: applications in organic synthesis.

Review 2. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

3. Direct C-F bond formation using photoredox catalysis.

4. Enantioselective organocatalytic alpha-fluorination of aldehydes.

5. Palladium-catalyzed regio- and enantioselective fluorination of acyclic allylic halides.

Review 6. Solar synthesis: prospects in visible light photocatalysis.

Review 7. Carbon-fluorine bond formation.

8. Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore.

9. Pd-catalyzed nucleophilic fluorination of aryl bromides.

10. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

1. Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

2. Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Review 3. Heterogeneous photocatalysis in flow chemical reactors.

4. δ-C-H Mono- and Dihalogenation of Alcohols.

5. Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

6. Photocatalytic Aminodecarboxylation of Carboxylic Acids.

7. Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

8. Decarboxylative Halogenation of Organic Compounds.

9. Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings.

10. Synthesis of α-Fluoro-α-Amino Acid Derivatives via Photoredox-Catalyzed Carbofluorination.