Synlett 2022; 33(19): 1948-1952
DOI: 10.1055/a-1938-1294
letter

Rhodium(I)-Catalyzed [2+2+1]-Carbonylative Cycloaddition of Diynes with Anthracene α-Diketone as the Source of CO

JingWen Jia
,
Yoshiko Yamaguchi
,
Tatsuya Ueda
,
,
Kiyomi Kakiuchi
,

This work was financially supported by the UBE Foundation for the Promotion of Science.


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Abstract

We report on the use of anthracene α-diketone as a source of carbon monoxide (CO) in carbonylation reactions. Photoirradiation by a 5 W blue LED of a diyne in the presence of anthracene α-diketone and a rhodium(I) catalyst resulted in a [2+2+1]-carbonylative cycloaddition of the diyne to CO released from the anthracene α-diketone to give a high yield (up to 99%) of the corresponding cyclopentadienone. This is the first demonstration of a CO-gas-free carbonylation reaction using anthracene α-diketone. Light irradiation was a major factor both in the generation of CO from anthracene α-diketone and in the catalytic activity. A halogen lamp, a fluorescent lamp, or sunlight also served as a light source for this reaction. With this system, there is no need for an additional reagent for generating CO.

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Publikationsverlauf

Eingereicht: 18. August 2022

Angenommen nach Revision: 07. September 2022

Accepted Manuscript online:
07. September 2022

Artikel online veröffentlicht:
11. Oktober 2022

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