Overall, all SPGs were stable under mild reaction conditions such as amide coupling, amine SN2, and acidic Boc deprotection. Similarly, under reductive amination and hydrogenation conditions, most SPGs demonstrated high stability. The oNB-R protecting group (5 and 5a) was partially reduced to the aniline under hydrogenation conditions and did not deprotect. It is worth noting that under hydrogenation conditions the PMB-R ( ) protecting group was stable. In reactions with harsher conditions, such as SNAr, Suzuki coupling, and ester hydrolysis, PMB-R, oNB-R and SES (4, 5, and 6) were superior to known SPGs, which degraded under these conditions. Only the SES protecting group was stable under Buchwald-Hartwig coupling conditions with potassium tert-butoxide as base. Switching the base, however, to cesium carbonate and Xantphos as ligand, resulted in a higher retention of oNB-R, 5. As a point of comparison, the parent sulfonyl fluoride ( ) only survived SN2, acidic deprotection, and amide coupling, highlighting the need for SPGs.