Practical Reactions / FGI

B(OH)2, Bpin → NH2

1
Add boronic acid (0.5 mmol, 1.0 equiv.) and N-Boc-Otosylhydroxylamine (1.5 equiv.) in 1, 2-dichloroethane (1 mL) to a round-bottom flask equipped with a magnetic stirring bar at room temperature.
2
Add trifluoroacetic acid (3 equiv.) to this stirred solution.
3
Stir the reaction mixture for 4 h and monitor the progress of the reaction by TLC.
4
Dilute the reaction mixture with ethyl acetate (10 mL) and wash with a saturated aqueous NaHCO3 solution (3 ×5 mL).
5
Wash the organic layer with brine solution (5 mL) and dry over anhydrous Na2SO4.
6
Obtain the product after removal of all of the volatiles.
7
Purify by a silica gel column chromatography using EtOAc/hexane as an eluent (hexane/ethyl acetate = 19:1, v/v).

Yield: 92%

2022
Metal-Free Direct Transformation of Aryl Boronic Acid to Primary Amines
10.1002/ejoc.202200508

[(1,1-Dimethylethoxy)carbonyl]azanyl 4-methylbenzenesulfonate / 105838-14-0