Table 1.
Reaction type |
Reactants |
Medium, pH conditions/catalysis |
Temperature, duration |
Ref. |
---|---|---|---|---|
ligation |
aliphatic/aromatic hydrazine analogues[a] |
aqueous, (mostly) alkaline |
25–35 °C, 24–72 h |
|
DMSO (anhydrous), Ar atmosphere |
50–60 °C, 4 days |
|||
|
|
|
|
|
|
hydroxylamines |
aqueous, acidic or DMAc/LiCl (2.5 % w/v), Et3N* |
40 °C, up to 700 h |
|
|
thiosemicarbazide |
aqueous, acidic |
60–65 °C, 90 min |
|
NMMO/water (80/20, v/v)* |
60 °C, 90 min |
|||
|
|
|
|
|
reductive amination |
1° amine ligands + reducing agent |
aqueous buffer, acidic or alkaline |
70 °C, 24–72 h |
|
MeOH/acetic acid |
50 °C, 12–16 h |
|||
DMF |
RT or 70 °C, 1 or 3 days |
|||
DMAc/LiCl* |
70 °C, 24 h |
|||
|
|
|
|
|
Pinnick oxidation & amide coupling |
1) NaClO2
|
1) aqueous, acidic |
1) RT, 20–48 h |
|
2) 1° amine ligands + coupling agents |
2) aqueous, pH switch to alkaline |
2) RT, 2 h–3 d |
||
|
aqueous, pH 5 |
4 °C, 24 h |
||
|
|
|
|
|
Knoevenagel condensation |
1,3‐diketones |
aqueous bicarbonate, pH 8.5 |
80–90 °C, 4–48 h |
[a] Characterized by hydrazine core (NH2‐NH‐R).