Executive Summary : | Bicyclo[1.1.1]pentanes (BCPs) hold considerable promise as structural leads in drug discovery programmes owing to the restricted conformation of their three-dimensional structure. Despite the growing number of synthetic strategies for the synthesis of 1,3-functionalized BCPs, the methods for accessing 1,2-functionalized BCPs, which are bioisosteres of 1,2-disubstituted benzene, are scarce. Consequently, the methods to synthesize 1,2-substituted BCPs are highly desirable and would be valuable for discovering new bioactive compounds. Photoredox catalysis has had an enormous impact on the field of organic synthesis as it enables new reactions to be achieved under mild conditions and, in many cases, enables reactions that otherwise would be highly difficult. The proposed project aims at the preparation of medicinally relevant 1,2-functionalized BCPs via 1,5-HAT-mediated processes under visible-light photocatalysis. To maximize the impact and application of the proposed strategies in organic synthesis, an asymmetric variant will also be developed to provide highly valuable enantioenriched BCPs. Furthermore, we also plan to develop a carbene C-H insertion strategy under visible light irradiation for the synthesis of fused BCPs that can be easily transformed into 1,2,3-tri functionalized BCPs. |