KBS24: Click coupling of azidomethylferrocene and bis propargyl 1,6 diaminohexane

KBS24 linear amine click coupling with azidomethylferrocene

Method

Copper sulfate pentahydrate (10.0 mg) and sodium ascorbate (23.2 mg) were dissolved in water (2 mL). Azidomethylferrocene KBS16 (58.2 mg, 0.241 mmol, 2.3 equiv.) dissolved in THF (1 mL) and bis-propargyl diaminohexane KBS17 (42 mg, 0.107 mmol) dissolved in THF (1 mL) were added to the flask. Additional water (1 mL) and THF (3 mL) were added and the mixture was stirred for 20 hours at room temperature. More sodium ascorbate (29 mg) was added and the reaction stirred for another 2 hours before ???

WORKUP

Characterisation

H NMR

KBS24-1 F5-7_1.zip KBS24-1 09-11-22.pdf

1H NMR (300 MHz, CDCl3) δ 7.49 (2H), 5.25 (4H), 4.39 (4H), 4.15-4.24 (18H), 3.18 (4H), 1.53 (2H), 1.43 (4H), 1.40 (18H), 1.19 (4H).

Partial assignment (using numbers from MestreNova prediction): δ 7.49 (triazole, 11 & 17), 5.25 (methylene, 34 & 48), 4.39 (methylene, 9 & 15), 4.15-4.24 (ferrocene, varied), 3.18 (hexane), 1.53 (hexane), 1.43 (hexane), 1.40 (boc groups), 1.19 (hexane).