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Meng, Qing-Yuan ; Schirmer, Tobias ; Berger, Anna Lucia ; Donabauer, Karsten ; König, Burkhard

Photocarboxylation of Benzylic C-H bonds

Article

Meng, Qing-Yuan , Schirmer, Tobias, Berger, Anna Lucia, Donabauer, Karsten and König, Burkhard (2019) Photocarboxylation of Benzylic C-H bonds. Journal of the American Chemical Society 141, pp. 11393-11397.

DOI to cite this document: 10.5283/epub.40471


Abstract

The carboxylation of sp(3)-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of ...

The carboxylation of sp(3)-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(1-phenylethyl)benzonitrile generated in situ. The resulting benzylic carbanion reacts with CO2 to generate the corresponding carboxylic acid after protonation. The reaction proceeded without the addition of any sacrificial electron donor, electron acceptor or stoichiometric additives. Moderate to good yields of the desired products were obtained in a broad substrate scope. Several drugs were successfully synthesized using the novel strategy.



Involved Institutions


Details

Item typeArticle
Journal or Publication TitleJournal of the American Chemical Society
PublisherAMER CHEMICAL SOC
Place of PublicationWASHINGTON
Volume141
Page Rangepp. 11393-11397
Date2019
Date of publication09 Jul 2019 08:59
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identification Number
ValueType
10.1021/jacs.9b05360DOI
KeywordsCARBON-DIOXIDE; VISIBLE-LIGHT; CATALYZED CARBOXYLATION; REDUCTION POTENTIALS; ALKENES; CO2; CARBONYLATION; RADICALS; HALIDES; SYSTEM;
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-404717
Item ID40471

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