As with any protecting group, broad stability is required. To provide insight for their use in any synthetic endeavor, the stability of SPGs was investigated in a variety of synthetic conditions. The top ten most used synthetic transformations in medicinal chemistry were chosen for SPG stability testing (Table ). These conditions included: amide coupling (HATU), SNAr (Et2N i Pr, 110 °C), acidic Boc deprotection (4 M HCl), ester hydrolysis (NaOH), Suzuki coupling (Pd(PPh3)4, K3PO4, 110 °C), amine SN2 (K2CO3), reductive amination (Na(CN)BH3), hydrogenation (Pd/C, H2), and Buchwald-Hartwig amination (Pd2(dba)3, P(o-tolyl)3, NaO t Bu, 100 °C). Model aryl protected sulfinates 1-6 and benzyl protected sulfinates 2a, 5a, and 6a, were added to the reaction mixture for a certain transformation, and upon completion of the reaction, the percentage of recovered SPG was calculated. Sulfonyl fluoride 7 was also subjected to these same conditions. The conditions chosen were the most common conditions found for each transformation. It is possible that in optimizing a reaction, one may find specific conditions that are less harsh and therefore result in greater retention of the SPG. In each transformation, the reaction itself proceeded in greater than 70% yield unless otherwise noted (see Supporting Information).