Similar to hydrogen bonds, as the strength of a halogen bond between a Lewis base and an R-X increases, the possibility of halonium (X + ) transfer via a transient halogen bond interaction also increases, with the R-X bond being broken and a new X-LB bond being formed 8d, 8s, 39 . Inspired by the possibility of F-cation transfer via the formation of a transient halogen bond derived from N-fluoropyridinium salt 1 , we set out to probe if this mechanism was viable and operating in the synthesis of racemic cis-4.