Synthesis of fluorinated azetidines enabled by photochemical strain released strategies

Azetidines are a very significant class of molecule in organic chemistry due to their good performance in drug discoveries campaign and their role as bioisosteres. Nevertheless, their current application is limited due to the harsh conditions often needed for their synthesis. The aim of this thesis is to develop a new synthetic pathway which implements photochemical reactions to synthetize fluorinated azetidines. Various azetidines were synthetized starting from strained azabyciclo butanes(ABBs) through a one-step difunctionalization protocol. The strategy involves an organic photocatalyst which operates via a reductive quenching mechanism. N-(trifluoromethylthio)phthalimide was used as a source of trifluoromethane thiolate, key intermediate to promote the opening of the ABB. The reaction conditions were optimized, and the mechanism was studied in order to obtain a better understanding of the reaction pathway. The generality of the reaction was tested on different substrates and further functionalization reaction was described as well.