Organophotoredox-catalyzed stereoselective reductive dimerization of chromone-2-carboxylic esters

The irradiation of chromone-2-carboxylic esters with a blue LED in the presence of Rose Bengal and triethanolamine (TEOA) is used to obtain 2,2′-bichromanone of methyl, ethyl, n -propyl, iso-propyl, n -butyl, n -pentyl, and n -hexyl chromone-2-carboxylic esters in 52-93% yield and dr trans  :  cis u...

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Bibliographic Details
Published in:New journal of chemistry 2024-01, Vol.48 (5), p.192-196
Main Authors: De, Arijit, Manna, Tanaya, Debnath, Subhas Chandra, Husain, Syed Masood
Format: Article
Language:English
Subjects:
Dimerization
Esters
Stereoselectivity
Triethanolamine
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Summary:The irradiation of chromone-2-carboxylic esters with a blue LED in the presence of Rose Bengal and triethanolamine (TEOA) is used to obtain 2,2′-bichromanone of methyl, ethyl, n -propyl, iso-propyl, n -butyl, n -pentyl, and n -hexyl chromone-2-carboxylic esters in 52-93% yield and dr trans  :  cis up to 83 : 17. The key role played by Rose Bengal, TEOA, and blue light was established through numerous control experiments and a plausible mechanism is discussed. The photodimerization of chromone-2-carboxylic esters in the presence of Rose Bengal and triethanolamine (TEOA) gives access to various alkyl substituted 2,2′-bichromanones.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj05659g