Photocatalytic Cascade Cyclization of Aryl Haloalkynyl Ketones Forming Cyclopenta[b]naphthalene Derivatives

An efficient metal-free, photoredox-mediated cascade cyclization of aryl 1-haloalk-5-ynyl ketones has been developed. Using catalytic amounts of eosin Y (EY) and EtNMe2 as a reductive quencher, various aryl 1-haloalk-5-ynyl ketones have been transformed into the corresponding cyclization products in up to 98% yield. As a result, synthetic access to differently alpha-functionalized cyclopenta[b]naphthones and direct construction of cyclopenta[b]naphtholes has been developed.

Automated summary

An efficient metal-free, photoredox-mediated cascade cyclization of aryl 1-haloalk-5-ynyl ketones has been developed. Using catalytic amounts of eosin Y (EY) and EtNMe2 as a reductive quencher, various aryl 1-haloalk-5-ynyl ketones have been transformed into the corresponding cyclization products in up to 98% yield. As a result, synthetic access to differently alpha-functionalized cyclopenta[b]naphthones and direct construction of cyclopenta[b]naphtholes has been developed.