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J Org Chem ; 88(13): 9094-9104, 2023 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-37314129

RESUMO

A photocatalyst- and additive-free visible-light-induced 6π-photocyclization of ortho-biaryl-appended ß-ketoesters has been developed. Upon irradiation with visible light, substrates undergo 6-endo-trig cyclization/1,5-H shift to 9,10-dihydrophenanthren-9-ols with high efficiency and selectivity. The reaction proceeds via conrotatory ring closure followed by a suprafacial 1,5-hydrogen shift leading to the observed single trans-fused products. Preliminary mechanistic studies reveal the feasibility of both 1,5-H shift and intersystem crossing of the diradical intermediate.


Assuntos
Hidrogênio , Luz , Ciclização
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