Pleasingly, when 2b was treated with BCB 1a in the presence of 2 mol% fac-Ir(ppy)3, the amidyl radical insertion product, 2-oxa-4-azabicyclo[3.1.1]hept-3-enes 3a, was obtained in 31% yield (entry 6). Further exploration with Lewis or Brønsted acids, such as Sc(OTf)3 and acetic acid, proved detrimental to product yield (entries 7 and 8). Replacing 2b with N-amidopyridinium iodide 2c did not yield the desired product (entry 9). Incorporation of methyl substituents on the pyridinium moiety proved beneficial in the reaction of such reagents with alkenes. Pleasingly, when we used N-amidocollidinium tetrafluoroborate 2d the desired product 3a was obtained in 36% yield (entry 10). Further optimization with different bases (entries 11-13) led to the highest yield of 3a (68%) when 2 equivalents of NaHCO3 were used with 2 equivalents of reagent 2d. Notably, 2-azabicyclo[1.1.1]pentane (3a') was not observed throughout the optimization process, possibly due to a high energy barrier associated with the nitrogen insertion into BCB. A reaction conditions-based sensitivity screening (Fig. and Supplementary Table ) showed that this protocol is only sensitive towards water content and high O2, whereas reaction concentration, temperature, and light intensity had minimal effect on the reaction outcome.