posted on 2021-12-21, 18:38authored byVeronika Schmalz, Ulrich Koert
A general synthetic
entry to functionalized dihydrophenalenes has
been found using naphthyl-cyclopropane esters as starting materials.
The desired annulation was possible with visible light, Ir(Fppy)3 as photocatalyst, BnNMe2 or DABCO as electron
donor, HAT-catalyst, and proton source. A broad scope of substituted
naphthyl and azanaphthyl derivatives provided the photoannulation
products in high yield. Deuteration studies support a photoredox mechanism
involving the photoreductive cyclopropane opening to an enolate radical
followed by an aryl radical trapping.