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Literature DB >> 18060156

Decarboxylative reduction of free aliphatic carboxylic acids by photogenerated cation radical.

Yasuharu Yoshimi¹, Tatsuya Itou, Minoru Hatanaka.

Abstract

The decarboxylation of free carboxylic acids was effected by a photogenerated cation radical of phenanthrene to yield the reduction product in the presence of a thiol, which provides an alternative method to the Barton decarboxylation procedure for aliphatic acids such as N-Boc amino acids.

Entities: Chemical

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Year: 2007 PMID： 18060156 DOI： 10.1039/b714526h

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

11 in total

1. Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.

Authors: John D Trzupek; Dongjoo Lee; Brendan M Crowley; Vasilios M Marathias; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2010-06-23 Impact factor: 15.419

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

Review 3. Dual Catalysis Strategies in Photochemical Synthesis.

Authors: Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal: Chem Rev Date: 2016-04-25 Impact factor: 60.622

4. Influence of solvent, electron acceptors and arenes on photochemical decarboxylation of free carboxylic acids via single electron transfer (SET).

Authors: Yasuharu Yoshimi; Shota Hayashi; Keisuke Nishikawa; Yoshiki Haga; Kousuke Maeda; Toshio Morita; Tatsuya Itou; Yutaka Okada; Nobuyuki Ichinose; Minoru Hatanaka
Journal: Molecules Date: 2010-04-12 Impact factor: 4.411

5. Picosecond to millisecond tracking of a photocatalytic decarboxylation reaction provides direct mechanistic insights.

Authors: Aditi Bhattacherjee; Mahima Sneha; Luke Lewis-Borrell; Omri Tau; Ian P Clark; Andrew J Orr-Ewing
Journal: Nat Commun Date: 2019-11-13 Impact factor: 14.919

6. Photoinduced Electron Transfer-Promoted Reactions Using Exciplex-Type Organic Photoredox Catalyst Directly Linking Donor and Acceptor Arenes.

Authors: Mugen Yamawaki; Akiko Asano; Toshiki Furutani; Yuki Izumi; Yosuke Tanaka; Kazuyuki Osaka; Toshio Morita; Yasuharu Yoshimi
Journal: Molecules Date: 2019-12-05 Impact factor: 4.411

Decarboxylative reduction of free aliphatic carboxylic acids by photogenerated cation radical.

1. Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.

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

Review 3. Dual Catalysis Strategies in Photochemical Synthesis.

4. Influence of solvent, electron acceptors and arenes on photochemical decarboxylation of free carboxylic acids via single electron transfer (SET).

5. Picosecond to millisecond tracking of a photocatalytic decarboxylation reaction provides direct mechanistic insights.

6. Photoinduced Electron Transfer-Promoted Reactions Using Exciplex-Type Organic Photoredox Catalyst Directly Linking Donor and Acceptor Arenes.

7. Redox mediators in visible light photocatalysis: photocatalytic radical thiol-ene additions.

8. Titania-promoted carboxylic acid alkylations of alkenes and cascade addition-cyclizations.

Review 9. Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis.

10. Phenylene-bridged bis(benzimidazolium) (BBIm²⁺): a dicationic organic photoredox catalyst.