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Thiasilacyclopentane (TSCP) and azasilacyclopentane (ASCP) heteroatom cyclics have proven capable of rapidly converting hydroxylated surfaces to functionalized surfaces in inorganic click reactions. In this work, we demonstrate that the use of these reagents can be extended to "simultaneous double-clicking" when both inorganic and organic substrates are present at the onset of the reaction. The simultaneous double-click depends on a first ring-opening click with an inorganic substrate that is complete in ∼1 s at 30 °C and results in the reveal of a cryptic mercaptan or secondary amine group, which can then participate in a second click with an organic substrate. TSCPs and ASCPs can take part in tandem double-click reactions in which the organic substrate is added to the reaction mixture after the initial inorganic click reaction is completed. Additionally, ASCPs with exocyclic functionality, specifically N -alkenyl-, N -aminoalkyl, and N -alkynyl-ASCPs, are shown to be options for tandem double-clicking in which functionalization proceeds in two independent steps and the sequence of the double-click reaction can be reversed.

Single-Molecule Orthogonal Double-Click Chemistry—Inorganic to Organic Nanostructure Transition