Visible-Light-Promoted 6π Photocyclization of ortho -Biaryl-Appended β-Ketoesters.
The Journal of organic chemistry(2023)
Abstract
A photocatalyst- and additive-free visible-light-induced 6π-photocyclization of -biaryl-appended β-ketoesters has been developed. Upon irradiation with visible light, substrates undergo 6--trig cyclization/1,5-H shift to 9,10-dihydrophenanthren-9-ols with high efficiency and selectivity. The reaction proceeds conrotatory ring closure followed by a suprafacial 1,5-hydrogen shift leading to the observed single -fused products. Preliminary mechanistic studies reveal the feasibility of both 1,5-H shift and intersystem crossing of the diradical intermediate.
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Key words
visible-light-promoted,biaryl-appended
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