Download Iron-Catalyzed Synthesis of Fused Aromatic Compounds via C–H by Arimasa Matsumoto PDF

By Arimasa Matsumoto

Iron catalysts in natural synthesis are strongly favorite simply because iron is non-toxic, low-cost and the main plentiful transition steel within the earth, even supposing their use remains to be restricted in comparison with that of infrequent, useful metals comparable to palladium, ruthenium and rhodium. This thesis describes the 1st sensible instance of iron catalysis within the carbon–hydrogen bond activation response to synthesized fused fragrant ring compounds. through the use of a different mix of iron catalyst and dichloride oxidant, quite a few form of naphthalene and phenanthrene derivatives have been synthesized through annulation response with alkynes together with direct C–H bond activation method. This fulfillment opens the recent risk of low-valent iron catalysis and expands artificial equipment for a sustainable society.

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The reaction mixture was stirred for an additional 1 h, then 1 mL of 1 M HCl (aq) and 5 ml of toluene were added. 7 Experimental Part 35 with toluene (5 mL 9 3). The combined organic layers were dried over sodium sulfate, and the volatiles were removed in vacuo. The remaining solid was dissolved in toluene and after a short-pass over silica gel (eluent = toluene), recrystallization from toluene/hexane afforded analytically pure product. The mother liquor was purified by silica gel column chromatography (eluent: hexane/ toluene = 20/1).

This selectivity was also observed in previous ironcatalyzed C–H bond activation reactions, and the presence of dichloride oxidant is important for this high selectivity [12]. Under these reaction conditions, an enyne was easily polymerized. This polymerization was attenuated by slow addition of the enyne, and (E)-9-phenyl-10-styrylphenanthrene was obtained in good yield with retention of the olefin geometry (entry 6). Similarly, trifluoromethylphenylacetylene (entry 7) gave the desired product in good yield when the alkyne was added slowly.

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