Table 1.
Azido iodination of alkenes 2a–f under flow conditions with polymer-bound bisazido iodate(I) complex 5.
 | ||||||
| entry | substrate | flow rate [mL/min] |
equiv 5a | product (racemic) |
yield flowb |
t, (yield) batchb |
| 1 |
 2a |
0.05 | 5 |
 3a |
98% | 15 h (97%) |
| 2 |
 2b |
0.04 | 5 |
 3b |
91% | 20 h (95%) |
| 3 |
 2c |
0.03 | 5 |
 3c |
61% | |
| 4 |
 2d |
0.02 | 5 |
 3d |
75% | |
| 5 |
 2e |
0.02 | 6 |
 3e |
78%c | |
| 6 |
 2f |
0.02 | 7 |
 3f |
70%d | |
aEquiv of 5 refers to the theoretical loading based on polymer-bound ammonium groups of Amberlyst A-26; bIsolated yields of pure products after evaporation of the solvent and in some cases followed by chromatographic purification; cContains about 12% starting material; dContains 15% of bisazido product.