To further demonstrate the compatibility and utility of germanyl alkynes in CuAAC reactions, we applied the CuAAC process to more challenging substrates. Using fluorophore-and cholesterol-derived azides, coupling with the triethyl germanyl alkyne delivered the expected products 26 and 27, respectively, in good yield, enabling possible downstream diversification of these functional of relevance to chemical biology (Scheme 3a). The utility of the germanyl triazole products was then assessed by subsequent derivatisation of exemplar compounds 15 and 21 (Scheme 3b). Chemoselective Suzuki-Miyaura cross-coupling of the BPin moiety in 21 was straightforward, giving 28 in excellent yield. Similarly, cross-coupling of the GeEt3 moiety in 15 under conditions developed by Schoenebeck and coworkers gave 29. Bromodegermanylation using NBS employing conditions from Schoenebeck gave bromotriazoles 30 and 31 in moderate to excellent yield. These could then undergo Suzuki-Miyaura cross-coupling to give 32 or chemoselective Negishi coupling to give 33. Finally, BPin 21 could be oxidised to the phenol derivative 34 or cross-coupled with piperidine under Chan-Lam conditions to give the aniline derivative 35 in good yield. In summary, we have demonstrated the first application of germanyl alkynes in CuAAC chemistry. These reagents are generally compatible but seem to be less reactive than other classes of alkyne. The germanyl alkyne CuAAC is applicable to functional group-rich molecules, opening opportunities for downstream diversification by chemoselective functionalisation strategies. The germanyl group installed in the triazole products can be used as a reactive handle for further diversification including cross-coupling reactions.