Next, we turned our attention to assess the scope of amidyl radical precursors 2 against BCB 1a (Fig. ). Amidyl radical precursors bearing a series of substituents with different electronic nature such as methyl-, phenyl, methoxy-, cyano-, bromo-, chloro-, trifluoromethyl-, and hydroxy-groups reacted smoothly to furnish the corresponding products 3o-3x in moderate to good yields (42-70%). Replacing phenyl ring of the amidyl radical precursor with 1,3-benzodioxole and naphthalene unit also afforded the desired products 3y and 3z in good yields (54% and 68%, respectively). Gratifyingly, heteroaromatic units such as pyridine, furan, and thiofuran are well tolerated in this protocol offering products 3aa-3ac in 51-71% yields. Furthermore, biologically relevant L-menthol and geraniol derivatives were successfully evaluated to afford the products 3ad and 3ae in 56% and 53% yield, respectively. Notably, no competitive reaction with the highly reactive trisubstituted alkene units of geraniol was noticed, highlighting the high chemoselectivity of amidyl radical reaction towards inter-bridgehead C1-C3 bond of BCB. Surprisingly, when acyl pyrazole-substituted BCB 1o was treated with 2d the spirocyclic product 5 was obtained in 47% yield (Fig. ), instead of a regular amidyl radical insertion product, probably due to the high nucleophilicity of pyrazole moiety, which could compete to react with the carbocationic intermediate 6 generated during the reaction. Monosubstituted and methyl-substituted BCBs found to be non-viable substrates (cf. 3ag and 3ah) for the current amidyl radical insertion reaction (Fig. ). Similarly, no desired products (3ai and 3aj) were obtained when aliphatic amidyl radical precursors were employed.