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Photocatalytic Dehydroformylation of Benzyl Alcohols to Arenes
Kolb, Daniel
, Almasalma, Ahmad A.
, Morgenstern, Martin
, Ganser, Leon
, Weidacher, Isabel
and König, Burkhard
(2023)
Photocatalytic Dehydroformylation of Benzyl Alcohols to Arenes.
ChemPhotoChem.
Date of publication of this fulltext: 05 Oct 2023 06:13
Article
DOI to cite this document: 10.5283/epub.54764
Abstract
In the last decades, many C-C bond-forming reactions have been developed, whereas less attention has been paid to the design of strategies involving C-C bond cleavage. We report a photocatalytic dehydroformylation sequence for the conversion of benzyl alcohols to arenes in a one-pot two-step process. Herein, the initial dehydrogenation of the benzyl alcohols to the corresponding benzaldehydes is ...
In the last decades, many C-C bond-forming reactions have been developed, whereas less attention has been paid to the design of strategies involving C-C bond cleavage. We report a photocatalytic dehydroformylation sequence for the conversion of benzyl alcohols to arenes in a one-pot two-step process. Herein, the initial dehydrogenation of the benzyl alcohols to the corresponding benzaldehydes is combined with an additional decarbonylation step yielding arenes. As a result, a broad range of benzyl alcohols can be easily transformed in short times under mild photocatalytic conditions. The conducted mechanistic studies indicate that our cooperative hydrogen atom transfer (HAT)-cobalt system proceeds through the formation of & alpha;-alkoxy- and acyl radicals as key intermediates, involving concomitant syngas (CO+H2) generation. The combination of photoinduced hydrogen atom transfer (HAT) and cobalt catalysis gives access to a mild dehydroformylation sequence for the defunctionalization of benzyl alcohols to arenes. The transformation proceeds through a stepwise radical pathway, wherein benzylic and acyl radicals are generated as key intermediates. As a result, stable C-C bonds can be cleaved while generating concomitant syngas (CO+H2).image
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| Item type | Article | ||||
| Journal or Publication Title | ChemPhotoChem | ||||
| Publisher: | WILEY-V C H VERLAG GMBH | ||||
|---|---|---|---|---|---|
| Place of Publication: | WEINHEIM | ||||
| Date | 7 September 2023 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identification Number |
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| Keywords | DECATUNGSTATE ANION; POLAR; photocatalysis; dehydroformylation; hydrogen atom transfer; cobalt; benzyl alcohols | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Yes | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-547642 | ||||
| Item ID | 54764 |
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