To facilitate bioorthogonal cleavage of rTCO-caged phenols while achieving high precursor stability, we envisioned the implementation of a self-immolative linker (SIL) that enables the use of carbamate linkages instead of ethers and carbonates. Here, we show that N,N'-dimethylethylenediamine (DMEDA) can be used as a minimal SIL to facilitate efficient bioorthogonal elimination of phenols (Fig. ). Depending on the structure of the Tz and the cleavable TCO we observed up to 96% release after 2 hours, while achieving high stability of the caged phenol under physiological conditions, as demonstrated by the design of a bioorthogonal prodrug with 700-fold reduced cytotoxicity.