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The photolysis of 1,1?-diacylferrocenes Fc(COR)2 (Fc = Ferrocenyl, R = CH3,Ph) in the presence of 1,10-phenanthroline (phen) in deoxygenated acetonitrile under irradiation with visible light has been studied. In these photolysis systems the phen has two important roles to play: one is to stabilize the photo-liberated Fe2+ by coordination, and the other is to promote the photolysis through photo-ligand exchange. Under this condition the photoproducts were isolated in definite composition and characterized by single crystal X-ray diffraction, 1H NMR spectroscopy, IR spectroscopy, photolysis-cyclic voltammetry and elemental analysis. The mechanism of the reactions was demonstrated to be charge transfer from metal to acylcyclopentadienyl ring, leading to cleavage of the bond between them. The phen attacks the Fe2+ ion to give the stable tris (1,10-phenanthroline) iron(II) complex cation and the acylcyclopentadienyl ring detaches from the Fe2+ ion, giving the enolate anion in the outer sphere of the complex. Crystallographic data for photoproduct 1, [Fe(phen)3] (C5H4COCH3)2 ·CH3CN ·2H2O: triclinic, space group P-1 (No. 2), a=12.714(4), b=13.125(3), c= 14.946(5) A, alpha=106.45(1), beta=112.13(3), gamma=79.60(2). V=2208(1) A3, R = 0.041, RW = 0.052. Crystallographic data for photoproduct 2, [Fe(phen)3](C5H4COC6H 5)2 ·0.5C6H6 ·H2O: triclinic, space group P-1 (No. 2), a= 12.218 (4), b= 12.440 (3), c= 16.989 (2) A, alpha = 98.56(2), beta= 102.06(2), gamma= 100.98(3), V=2431(2) A3, R = 0.049, RW = 0.057.
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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion