Green Chemistry Approaches to Condensation Reactions of Formylferrocene with Active Methylene Containing Compounds

Abstract

The condensation reactions of formylferrocene with active methylenecontaining compounds were achieved by microwave irradiation, grinding or heating in water, in moderate to good yields. The structures were confirmed by 1 H NMR, 13 C NMR, IR spectra, and elemental analyses.

5-Ferrocenylmethyl-2,2-dimethyl-5-(prop-2-ynyl)-1,3-dioxane-4,6-dione

“…(1) 5-Ferrocenylmethylene-2,2-dimethyl-1,3-dioxane-4,6dione (2.50 g, 7.34 mmol) (Bai et al, 2004) in MeOH (80 ml) was hydrogenated (3 atm) for 30 min at room temperature using Pd/C (0.24 g, 5 wt.% Pd) as catalyst. Crystallization from MeOH yielded a brown product (1.66 g, 66%).…”

Synthesis of ferrocenoate esters, amides and other ferrocenoyl derivatives using ferrocenoyl fluoride. A comparison of the reactions of ferrocenoyl fluoride in [bmim][BF4] with the microwave-promoted solvent-free reactions of ferrocenoyl fluoride

“…In many cases, ferrocene derivatives have been synthesized in alternative reaction media to volatile organic solvents. Examples include ionic liquids [2][3][4], inorganic supports [5][6][7][8][9][10] or under solventfree conditions [11][12][13][14][15][16][17]. The solubility of ferrocenes has also been investigated in supercritical fluids [18], and some highly fluorinated ferrocenes have been synthesized for the fluorous phase technique [19].…”