Remote Giese Radical Addition by Photocatalytic Ring Opening of Activated Cycloalkanols
Noelia Salaverri, Benedetta Carli, Patricia B. Gratal, Leyre Marzo, José Alemán
Abstract
Abstract The application of proton coupled electron transfer (PCET) processes in organic synthesis has opened the door to new radical intermediates for synthesis such as alkyl radicals in remote positions to a ketone. Herein, we present the addition of these remote alkyl radicals to electron deficient double bonds under photoorganocatalyzed and very mild conditions. The method is not only applicable to diactivated double bonds, but monoactivated ones are also accessible using more stabilized alkyl radicals, and alkyl chains of any length can be introduced. The final products can be easily converted into more complex structures via a one‐pot process, and the activating functional groups were transformed in the more versatile methyl esters. Mechanistic investigations support a mechanistic proposal based on a PCET process. magnified image