Given the potential to react with complex and functional biomolecules under mild conditions, we next reacted phenol 131 with alkyl halides to install propargylic, allyl, ester and amine functionality to enable potential application as linkers, generating OSF reagents 134-137 (Scheme 6a). Allyl and ethyl ester OSFs (135, 136) were further characterized by X-ray crystallography (see SI for structures). Alternatively, the phenol was treated with Tf2O to afford aryl triflate 138 which was applied to palladium-catalyzed deoxygenation and chlorination reactions to generate OSFs 139 and 140. Propargylic OSF 134 readily reacted with serine methyl ester hydrochloride to provide amino-oxetane 142 in 63% yield (Scheme 6b). The propargylic ether was then demonstrated to undergo CuAAC under standard conditions (143). Allyl OSF 135 reacted similarly through a deFS pathway with an adenosine derivative (144).