Experimental study demonstrates electroreductive coupling of chromones with benzophenones, highlighting versatile pathways to synthesize diarylmethylchromones and tetrasubstituted furans.
The electroreductive coupling of chromones with benzophenones in the presence of TMSCl gave adducts reacted at the 2‐position of chromones as trimethylsilyl ethers. From 3‐methyl‐ and 3‐phenylchromones, 2,3‐cis‐adducts were formed predominantly. The cis‐adducts were isomerized to trans‐ones by treatment with DBU. The detrimethylsilylation of the adducts with 1 M HCl aq/dioxane produced the corresponding alcohols. The dehydrosiloxylation of the adducts or dehydration of the desilylated alcohols brought about 2‐diarylmethylchromones. The detrimethylsilylation of the adducts with TBAF and subsequent treatment with NaH afforded ring‐opening products. The dehydration of the ring‐opening products obtained from 3‐methyl‐ and 3‐phenylchromons brought about tetrasubstituted furans or dihydrobenzofuran‐3‐ones. The dehydrogenation of the adducts with DDQ and subsequent desilylation with 1 M HCl aq/dioxane gave 2‐(diarylhydroxymethyl)chromones.
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Kise et al. (2019) studied this question.
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