Boc₂O Selection Cannot Be Judged by Protection Installation Alone: Experimental Decision-Making from Substrate Nucleophilicity and Medium Effects to Deprotection Pathways

The most common use of Boc₂O [di-tert-butyl dicarbonate] is to convert amines into Boc [tert-butyloxycarbonyl]-protected carbamates. In practical synthesis, however, deciding whether Boc₂O is appropriate cannot be based solely on whether the Boc group can be introduced smoothly at that step.