Radical Carbosulfonylation of Propellane: Synthesis of Sulfonyl β-Keto-bicyclo[1,1,1]pentanes

The construction of multiply functionalized bicyclo[1.1.1]pentanes (BCPs) is of high synthetic value, as they are frequently harnessed as bioisosteres of 1,3-disubstituted benzene rings, alkynes, and tert-butyl groups in medicinal chemistry. Herein, we disclose a practical radical-mediated carbosulfonylation of propellane for the synthesis of sulfonyl beta-keto-substituted BCPs by using vinyl sulfonates as dual-function reagent. This protocol features broad functional group tolerance and excellent atom-economy, leading to a variety of valuable difunctionalized BCP derivatives under mild photochemical conditions.

Automated summary

The study presents a method for synthesizing sulfonyl beta-keto-substituted BCPs through a carbosulfonylation reaction, using vinyl sulfonates as dual-function reagent, with broad functional group tolerance and excellent atom-economy under mild photochemical conditions.