Ethylenediamine → 4-Iodobiphenyl

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (19.5 mg, 0.102 mmol, 10 mol %), 4-bromobiphenyl (234 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ethylenediamine (13.5 μL, 0.202 mmol, 20 mol %) and sulfolane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 23 h. The resulting suspension was allowed to reach room temperature, poured into hexane (20 mL) and washed with water (3×20 mL). The combined organic phases were dried (MgSO4), concentrated, and the residue was purified by flash chromatography on silica gel (hexane) to provide 262 mg (94% yield) of 4-iodobiphenyl as white crystals.

Provenance & Evidence