Reactions of Fe3(CO)12 with 2-methyl-3-butyn-1-ol and 3-pentyn-1-ol under basic methanolic conditions: The crystal structures of Fe2(CO)6(μ-CO)(μ-η2-[HCC{C(CH3)2}C(O)(OCH3)]) and of (μ-H)Fe3(CO)9(μ3-η3-[H3CCC(CH2)(CH2)CO])

Bertolotti, Federica; Gervasio, Giuliana; Marabello, Domenica; Sappa, Enrico; Secco, Andrea

doi:10.1016/j.jorganchem.2008.04.045

Cited by 6 publications

(1 citation statement)

References 46 publications

(17 reference statements)

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“…To the best of our knowledge, none of the numerous diiron complexes containing unsaturated C 3 ligands, including bridging allenylidene complexes, can properly account for the possible involvement of 3a in catalytic propargylic substitution . As an example, no propargylic susbstitution is observed in the reaction of alkynols and MeOH with Fe 3 (CO) 12 , in spite of the formation of bridging allenylidene intermediates; the result is a rather complex rearrangement of the bridging ligand with incorporation of a CO …”

Section: Resultsmentioning

confidence: 98%

Ferrocenes Containing a Pendant Propargylic Chain Obtained via Addition of Propargyl Alcohol to μ-Vinyliminium Ligands in Diiron Complexes

et al. 2011

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The diiron bridging vinyliminium complexes [Fe 2 {μ-η 1 :η 3 -CN(Me) 2 C(R′)C(R″)}(μ-CO)(CO)-(Cp) 2 ][SO 3 CF 3 ] (R′ = H, R″ = SiMe 3 , 3a; R′ = H, R″ = Tol =4-MeC 6 H 4 , 3b; R′ = Me, R″ = Me, 3c; R′ = SPh, R″ = Me, 3d; R′ = H, R″ = Fc = [Fe(C 5 H 4 )(Cp)], 6e) react with propargyl alcohol (HCCCH 2 OH), in refluxing toluene, affording the polysubstituted ferrocenes as mixtures of two isomeric forms: [1-NMe 2 -2-R′-3-R″-5-CH 2 OCH 2 CCH-Fc] (R′ = H, R″ = SiMe 3 , 6a; R′ = H, R″ = Tol, 6b; R′ = Me, R″ = Me, 6c; R′ = SPh, R″ = Me, 6d, R′ = H, R″ = Fc, 6e) and [1-NMe 2 -2-R′-3-R″-4-CH 2 OCH 2 CCH-Fc] (R′ = H, R″ = SiMe 3 , 7a; R′ = H, R″ = Tol, 7b; R′ = Me, R″ = Me, 7c; R′ = SPh, R″ = Me, 7d) in overall yields of about 55−65%. Formation of the functionalized cyclopentadienyl in the ferrocene products takes place through the assembly of two propargyl units with the bridging vinyliminium ligand: one alkynol is incorporated by a [3 + 2] cycloaddition with the bridging C 3 ligand; a second alkynol unit gives rise to a pendant chain through −OH substitution. Investigations show that the substitution step is catalyzed by the parent diiron complex itself or by a mononuclear iron fragment (likely the Fp + complex). The pendant propargyl chain has been exploited to connect the ferrocene to other molecular fragments: in particular, the reaction of 6a with 4-biphenyl azide, by copper-catalyzed azide−alkyne cycloaddition (CuAAC), leads to the formation of the triazole-functionalized ferrocene [1-NMe 2 -2-CH 2 OCH 2 -N 3 (C 6 H 4 Ph)C 2 H-4-SiMe 3 -Fc] (12). Moreover, 6a reacts with Co 2 (CO) 8 , affording the complex [Co 2 {μ-η 2 -HC CR}(CO) 6 ] (13), (HCCR = 6a), where the alkyne adopts a η 2 coordination to a dicobalt hexacarbonyl fragment. The molecular structure of 7a has been determined by X-ray diffraction studies.

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Section: Resultsmentioning

confidence: 98%

Ferrocenes Containing a Pendant Propargylic Chain Obtained via Addition of Propargyl Alcohol to μ-Vinyliminium Ligands in Diiron Complexes

et al. 2011

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Microwave‐Assisted Aminocarbonylation of Ynamides by Using Catalytic [Fe₃(CO)₁₂] at Low Pressures of Carbon Monoxide

Pizzetti

Russo

Petricci

2011

Chemistry A European J

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The microwave-assisted aminocarbonylation of ynamides at low pressures of CO is reported. A new class of (E)-acrylamides that are potentially suitable for several applications has been regioselectively synthesized after microwave irradiation for only 20 min by using eco-friendly [Fe(3)(CO)(12)] as the catalyst precursor and triethylamine as the ligand. This transformation is atom economic as all reactants are used in stoichiometric quantities. Furthermore, the transformation is efficiently applied to the alkoxycarbonylation of alkynes as well. Moreover, running these reactions under microwave irradiation allows the simplification of the reaction conditions with remarkable reductions in time, temperature and gas pressure.

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Iron Cluster Compounds: Compounds With Hydrocarbon Ligand

Mathur¹,

Misra²

2019

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Reactions of Fe3(CO)12 with 2-methyl-3-butyn-1-ol and 3-pentyn-1-ol under basic methanolic conditions: The crystal structures of Fe2(CO)6(μ-CO)(μ-η2-[HCC{C(CH3)2}C(O)(OCH3)]) and of (μ-H)Fe3(CO)9(μ3-η3-[H3CCC(CH2)(CH2)CO])

Cited by 6 publications

References 46 publications

Ferrocenes Containing a Pendant Propargylic Chain Obtained via Addition of Propargyl Alcohol to μ-Vinyliminium Ligands in Diiron Complexes

Ferrocenes Containing a Pendant Propargylic Chain Obtained via Addition of Propargyl Alcohol to μ-Vinyliminium Ligands in Diiron Complexes

Microwave‐Assisted Aminocarbonylation of Ynamides by Using Catalytic [Fe₃(CO)₁₂] at Low Pressures of Carbon Monoxide

Iron Cluster Compounds: Compounds With Hydrocarbon Ligand

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Reactions of Fe3(CO)12 with 2-methyl-3-butyn-1-ol and 3-pentyn-1-ol under basic methanolic conditions: The crystal structures of Fe2(CO)6(μ-CO)(μ-η2-[HCC{C(CH3)2}C(O)(OCH3)]) and of (μ-H)Fe3(CO)9(μ3-η3-[H3CCC(CH2)(CH2)CO])

Cited by 6 publications

References 46 publications

Ferrocenes Containing a Pendant Propargylic Chain Obtained via Addition of Propargyl Alcohol to μ-Vinyliminium Ligands in Diiron Complexes

Ferrocenes Containing a Pendant Propargylic Chain Obtained via Addition of Propargyl Alcohol to μ-Vinyliminium Ligands in Diiron Complexes

Microwave‐Assisted Aminocarbonylation of Ynamides by Using Catalytic [Fe3(CO)12] at Low Pressures of Carbon Monoxide

Iron Cluster Compounds: Compounds With Hydrocarbon Ligand

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Microwave‐Assisted Aminocarbonylation of Ynamides by Using Catalytic [Fe₃(CO)₁₂] at Low Pressures of Carbon Monoxide