Literature DB >> 25068198

Photocatalytic decarboxylative reduction of carboxylic acids and its application in asymmetric synthesis.

Carlo Cassani1, Giulia Bergonzini, Carl-Johan Wallentin.   

Abstract

The decarboxylative reduction of naturally abundant carboxylic acids such as α-amino acids and α-hydroxy acids has been achieved via visible-light photoredox catalysis. By using an organocatalytic photoredox system, this method offers a mild and rapid entry to a variety of high-value compounds including medicinally relevant scaffolds. Regioselective decarboxylation is achieved when differently substituted dicarboxylic acids are employed. The application of this method to the synthesis of enantioenriched 1-aryl-2,2,2-trifluoroethyl chiral amines starting from natural α-amino acids further testifies to the utility of the developed photocatalytic decarboxylative reduction protocol.

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Year:  2014        PMID: 25068198     DOI: 10.1021/ol5019294

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


  16 in total

1.  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

2.  Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.

Authors:  Tian Qin; Lara R Malins; Jacob T Edwards; Rohan R Merchant; Alexander J E Novak; Jacob Z Zhong; Riley B Mills; Ming Yan; Changxia Yuan; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-16       Impact factor: 15.336

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

Authors:  Joel W Beatty; James J Douglas; Richard Miller; Rory C McAtee; Kevin P Cole; Corey R J Stephenson
Journal:  Chem       Date:  2016-09-08       Impact factor: 22.804

4.  Photocatalytic Aminodecarboxylation of Carboxylic Acids.

Authors:  Simon B Lang; Kaitie C Cartwright; Richard S Welter; Theresa M Locascio; Jon A Tunge
Journal:  European J Org Chem       Date:  2016-06-19

5.  An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors.

Authors:  Tyler A Wilson; Pratibha C Koneru; Stephanie V Rebensburg; Jared J Lindenberger; Matthew J Kobe; Nicholas T Cockroft; Daniel Adu-Ampratwum; Ross C Larue; Mamuka Kvaratskhelia; James R Fuchs
Journal:  ACS Med Chem Lett       Date:  2019-01-30       Impact factor: 4.345

6.  Total Synthesis of (+)-Arborisidine.

Authors:  Zhiyao Zhou; Alison X Gao; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2019-05-02       Impact factor: 15.419

7.  α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

Authors:  Mirna El Khatib; Ricardo Augusto Massarico Serafim; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-23       Impact factor: 15.336

8.  Photoredox catalysis in a complex pharmaceutical setting: toward the preparation of JAK2 inhibitor LY2784544.

Authors:  James J Douglas; Kevin P Cole; Corey R J Stephenson
Journal:  J Org Chem       Date:  2014-11-17       Impact factor: 4.354

9.  Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis.

Authors:  Giulia Bergonzini; Carlo Cassani; Carl-Johan Wallentin
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

10.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

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