Light-Driven Synthesis and Functionalisation of Bicyclopentanes (BCPs)

In this thesis it will be discussed the synthesis of difluoroalkyl bicyclopentanes, hybrid bioisosters coming from the radical reaction between the difluoromethylene group and the [1.1.1]- or [3.1.1.]-propellane group, used respectively to replace ketones or ethers groups and benzene. An organic photocatalyst catalizes this reaction, forming an electrondonor acceptor (EDA) complex with the reagent. After being excited by light, a difluoromethylene radical will be generate and will react with the propellane following an atom-transfer radical addition (ATRA). The structure of organophotocatalyst will determine the type of excited state, local or charge-transfer (CT). Bicyclopentanes have shown improved potency and pharmacocinetiks compared to their bioisosters and are worth studying new routes to synthesize them.