Taking advantage of the simplicity of the reaction protocol, we performed a sequence of cyclopropanation/ring-expansion directly from norbornene derivative 8a (Scheme 4C). Without the need to purify the cyclopropane intermediate, we were delighted to observe the formation of product 6a in 55% and 7j in 45% overall yield. Overall, through only small changes in reaction conditions, we could access both saturated and unsaturated products resulting from a one carbon insertion. The same reductive telescoped process was also successful for both linear and bicyclic cyclopropanes, resulting in ring opening products 7p and 7e in 48% and 41% overall yield respectively (Scheme 4D). In some cases, we observed an over reduction of the carbonyl group to give the corresponding alcohol. Considering that the alcohol could be a suitable precursor for the removal of the acyl group via a further C-C bond cleavage step, we performed the reaction from cyclopropane 3a with 5 equivalents of phenyl disulfide (Scheme 4E). In this case, 51% of alcohol 9 was isolated. The conversion of 9 into ether 10 in 80% yield has been reported, demonstrating the possibility for acyl group removal, which can therefore be considered as a transient activating group for the cyclopropane. Based on our reported preliminary results on the [3+2] annulation under photocatalyst free conditions (Scheme 2A), we then further explored the scope of disubstituted cyclopropane substrates (Scheme 5). This protocol is especially attractive due to its simplicity, as no catalyst, Lewis or Brønsted acid or other additive is required, in contrast to other reported methods. The best yields were obtained with 5 equivalents of alkynes as trapping reagents under irradiation for 48 hours (see SI for optimization).