Benzyl Alcohol Functionalization of [1.1.1]Propellane with Alkanes and Aldehydes
Fei Li1,2,3, Jianyang Dong1, Chenya Wang1
1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, China.
Abstract:
Bicyclo[1.1.1]pentanes (BCPs) play a crucial role in drug discovery research as C(sp3)-rich bioisosteres of benzene rings. However, the preparation of BCPs with strong alkane C(sp3)-H bonds has not been reported to date. In this study, we reported a method for light-induced benzyl alcohol functionalization of [1.1.1]propellane with aliphatic hydrocarbons (which have not previously been explored for this purpose) and aldehydes under metal- and photocatalyst-free conditions. The BCP products could be transformed into various useful derivatives, demonstrating the utility of the method. Notably, we achieved the synthesis of functionalized BCPs with simple alkanes.
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