Moving from propynyl BMIDA 2a to phenylacetylenyl BMIDA 2b was less straightforward than expected. The optimal conditions for 2a delivered only 16% of 2-BMIDA-3phenylindole (4) when using 2b (entry 5) and an independent optimization was necessary (see SI). Ultimately this required the use of N-acyl 2-iodoaniline (1b) under the more classical Larock conditions for this aryl-substituted alkyne, giving 4 in good yield (entry 6). The origin of this difference in reactivity is uncertain but the increased steric bulk of alkyne 2b is very likely to dominate, with electronic effects also a minor contributor. These conditions were subsequently assessed for generality across a series of annulations (Scheme 2). A series of alkyl alkynes were successfully accommodated to generate a small library of 2-BMIDA-3-alkyl indole products in good to excellent yield (Scheme 2a). The alkyl-substituted BMIDA alkyne progenitors were accessed via a metalation/borylation sequence using the requisite alkyl alkyne (see SI). Compound 19 was delivered in low yields under the PdCl2(dppf) general conditions; however, this was found to improve when using the ligand-free conditions developed for the aryl/alkenyl alkynes -the origin of this subtle substrate divergence remains unclear.