## 2 Results
### CuAAC Reactions in Flow
14 umol of copper), to give a set of identical flow reactors **R1**-**R5**. In this case, pumping was effected by a gas-tight syringe, used for the preliminary flushing of devices with 0.7% sodium l-ascorbate in aqueous MeOH and, after turning of the catalyst bed to pale-yellow, of the solution of reactants and internal standards. The testing of **R1** and **R2** in the benchmark reaction was performed in MeOH-THF (4:1) and MeOH-H\({}_{2}\)O (4:1), respectively, with the devices being placed in a glove-bag filled with N\({}_{2}\). The two rather long runs (\(S\)/\(C\) \(\sim\) 350 each) were carried out in parallel with a dual channel syringe pump, \begin{table}
\begin{tabular}{c c c c c c c c c} \hline \hline
**Entry \({}^{\ast}\)** & **Device Type** & **Reducing** & **Solvent** & \(S\)/\(C\)\({}^{\ast}\) & \(T\) & \(\mathrm{\upmu}\) & \(\mathrm{\upmu}\) & \(\mathrm{\upmu}\) & \(\mathrm{\upmu}\) \\  & **(length/cm)** & **agent \({}^{\mathrm{b}}\)** & **(volume ratio)** & & \(\mathrm{\upmu}\) & \(\mathrm{\upmu}\) & (\(\mathrm{\upmu}\), \(\mathrm{\upmu}\)) & (\(\mathrm{\upmu}\), \(\mathrm{\upmu}\)) & (\(\mathrm{\upmu}\), \(\mathrm{\upmu}\)) & (\(\mathrm{\upmu}\), \(\mathrm{\upmu}\)) & (\(\mathrm{\upmu}\), \(\mathrm{\upmu}\), \(\mathrm{\upmu}\)) & (\(\mathrm{\upmu}\), \(\mathrm{\upmu}\), \(\mathrm{\upmu}\)) \\ \hline
1 & MCFR (15) & HQ & THF & 5.0 & 24 & 0.6 & 190 & \(<\)5 & - \\
2 & MCFR (15) & PH & THF & 5.0 & 24 & 0.4 & 280 & 8 & \(<\)2 \\
3 & MCFR (10) & ASC & MeOH/THF (4:1) & 67 & 24 & 1.5 & 48 & \(>\)99 & 34 \\
4 & MCFR (10) h & (ASC) & MeOH/THF (4:1) & 16 & 24 & 12.0 & 6 & 27 & 74 \\
5 & MCFR (10) h & (ASC) & MeOH/THF (4:1) & 16 & 24 & 6.0 & 12 & 38 & 52 \\
6 & MCFR (10) h & (ASC) & MeOH/THF (4:1) & 47 & 24 & 3.0 & 24 & 74 & 51 \\
7 & MCFR (10) h & (ASC) & MeOH/THF (4:1) & 77 & 24 & 1.5 & 48 & 99 & 34 \\
8 & PCFR (15) h & HQ & THF & 5.3 & 24 & 0.6 & 205 & \(<\)5 & - \\
9 & PCFR (15) h & PH & THF & 5.3 & 24 & 0.4 & 310 & 47 & 4 \\
10 & PCFR (15) h & ASC & MeOH/THF (4:1) & 7.2 & 24 & 6.0 & 19 & 57 & 70 \\
11 & PCFR (15) h & (ASC) & MeOH/THF (4:1) & 6.5 & 60 & 3.0 & 39 & \(>\)99 & 60 \\
12 & PCFR (15) h & (ASC) & MeOH/THF (4:1) & 6.5 & 60 & 3.0 & 39 & 89 & 53 \\
13 & PCFR (15) h & (ASC) & MeOH/THF (4:1) & 6.5 & 60 & 3.0 & 39 & 97 & 58 \\
14 & PCFR (15) h & (ASC) & MeOH/THF (4:1) & 6.5 & 60 & 3.0 & 39 & 91 & 55 \\
15 & PCFR (15) h & (ASC) & MeOH/THF (4:1) & 6.5 & 60 & 3.0 & 39 & 85 & 51 \\ \hline \hline \end{tabular} \({}^{\mathrm{a}}\) Conditions: benzylazide and proparyl alcohol (0.2 M each) in the indicated solvent (2.5–24 mL). \({}^{\mathrm{b}}\) HQ = before the CuAAC run, the reactor was flushed with 0.1 M hydquinone in THF (3 equiv.). \({}^{\mathrm{c}}\) PH = phenylhydrazine (3 equiv. vs. Cu) added to the solution of the reactants; ASC = before the CuAAC run, the reactor was flushed with 10 mL saturated sodium l-ascorbate (approx. 8 equiv. vs. Cu) in MeOH/H\({}_{2}\)O (9:1) (ASC) = reactant stream saturated with sodium l-ascorbate. \({}^{\mathrm{c}}\) Ratio \(n_{\mathrm{\pi}ad}\)/\(n_{\mathrm{Cu}}\) at the end of the run, calculated on the basis of the initial metal content in the reactor. \({}^{\mathrm{d}}\) Flow-rate. \({}^{\mathrm{e}}\) Estimated average residence time of the reactants in the catalyst-filled section. \({}^{\mathrm{f}}\) Conversion extent of the azide shown by GC-MS with \(n\)-nonane or \(m\)-xylene as the internal standard. \({}^{\mathrm{g}}\) Space-time yield. \({}^{\mathrm{h}}\) Reactor from the previous run.  
\end{table} 
Table 2: Continuous-flow CuAAC runs in the monolithic (MCFR) and packed-bed (PCFR) devices based on reduced **M7**-Cu(OT)\({}_{2}\). with simultaneous variation of the flow-rates in the range \(\phi\) = 0.6-1.8 mL h\({}^{-1}\) (Table 3, entries 1 and 3). Because the former solvent mixture turned-out to lead to higher conversion degrees, all of the subsequent experiments made use of mixtures of MeOH and THF as the reaction medium.