Palladium-catalyzed reaction of 2-iodoferrocenyl alcohols with internal alkynes: Synthesis of functionally 1,2-disubstituted ferrocenes and ferroceno-pyrans

Yucel, Baris; Şanlı, Bahar; Soylemez, Huseyin; Akbulut, Hüseyin

doi:10.1016/j.jorganchem.2012.01.007

Cited by 9 publications

(7 citation statements)

References 106 publications

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“…1-ferrocenyl ethanol [16], 1-ferrocenyl-1,3-butanedione [15a] and 1-(4methoxyphenyl)butane-1,3-dione [17] were synthesized according to the procedures reported in the literature. Melting points were measured in evacuated capillaries and were not corrected.…”

Section: General Experimental Methodsmentioning

confidence: 99%

“…Both diastereomeric forms are related by a symmetry plane with inversion of the configuration at each carbon. 101.219(3) C(16)-C 171.502(2) 1.501 111.469(3) Fe(1)-C(Cp) avg 2.0433 2.0524 2.046 Fe(1)-C(Cp') avg 2.0468 2.0504 2.047 Angles C(10)-C(11)-C 13110.63 13108.6(6) 110.57(19) C(11)-C(13)-C 14112.43 13112.0 7110.92(19) C(11)-C(13)-C (16) 110.15 13111.4 6113.34 19) C(14-C(13)-C (16) 106.99 13105.6 7107.39(19) C(13)-C 14-O 1122.00 15119.8(8) 120.4(2) C(13)-C(16)-O 2120.64 (16) 120.7 7121.7(2) Abbreviations: Cp = C 5 H 5 , Cp' = C 5 H 4 .…”

Section: X-ray Crystallographic Studiesmentioning

confidence: 99%

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Synthesis, characterization and X-ray crystal structures of chiral ferrocene-containing β-diketones

Ahumada

Roisnel

Sinbandhit

et al. 2013

Journal of Organometallic Chemistry

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CCDC 922490, 922491, and 922492 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.International audienceThree new chiral ferrocene-containing β-diketones have been synthesized by reacting 1-ferrocenyl ethanol with the corresponding 1,3-diketone reagent MeCOCH2COR (R = Me, 4-C6H4OMe, Fc; Fc = (η5-C5H5)Fe(η5-C5H4)), using cerium(IV) ammonium nitrate (CAN) mediated C-C bond formation. These compounds identified as 3-(1-ferrocenylethyl)-pentane-2,4-dione (1), 1-(4-methoxyphenyl)-2-(1-ferrocenylethyl)-butane-1,3-dione (2), and 1-ferrocenyl-2-(1-ferrocenylethyl)-butane-1,3-dione (3), have been isolated as air and thermally stable microcrystalline solids in 79, 63 and 44% yields, respectively. Compounds 2 and 3 were formed in 63:37 and 88:12 diastereomeric ratios, respectively. They have been fully characterized by elemental analyses, FT-IR spectra, mass spectrometry, and their complete assignments have been conducted using 2D NMR experiments. In addition, their molecular identity and geometry have been confirmed by single-crystal X-ray diffraction, and both solution and solid state measurements have shown that the three complexes exist solely as their diketo tautomers

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Section: General Experimental Methodsmentioning

confidence: 99%

Section: X-ray Crystallographic Studiesmentioning

confidence: 99%

Synthesis, characterization and X-ray crystal structures of chiral ferrocene-containing β-diketones

Ahumada

Roisnel

Sinbandhit

et al. 2013

Journal of Organometallic Chemistry

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“…We therefore decided to start the synthesis of the imidazolium salts from commercially available N , N ‐(dimethylaminomethyl)ferrocene. By using a modified procedure from Plenio et al11 and Yucel et al,12 this reagent can easily be functionalised by lithiation in diethyl ether at room temperature followed by reaction of the lithiated species with iodine at –78 °C. 1‐Iodo‐2‐(dimethylaminomethyl)ferrocene ( 1 ) was obtained in 64 % yield as a moderately stable oily solid (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Bifunctional N‐Heterocyclic Carbene Ferrocenyl Ligands – Synthesis and Palladium(II) Complexes

et al. 2015

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“…Unsymmetrical alkynes gave rise to product mixtures. 93 Functionalized 1′-substituted iodoferrocenes such as 146 have been shown by Nijhuis et al to undergo a Heck reaction with vinylferrocene (147), giving trans-diferrocenylethene derivatives such as 148 with an extended π system in up to 81% yield with the Pd(OAc) 2 /MePhos catalyst system (MePhos = 2-dicyclohexylphosphino-2′-methylbiphenyl) (Scheme 48). 94 The synthesis of a particularly extended ferrocenebased π system was reported by Senge et al, who performed a double Suzuki coupling of borylated porphyrins such as 149 with 1,1′-diiodoferrocene (44) to afford substituted ferrocenes such as 150 in 37% yield.…”

Section: Palladium-catalyzed Reactions Of Haloferrocenesmentioning

confidence: 99%

Haloferrocenes: Syntheses and Selected Reactions

Butenschön

2018

Synthesis

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Although haloferrocenes constitute important starting materials for many ferrocene-derived products with importance in a variety of fields such as materials science, medicinal chemistry and catalysis, only relatively few haloferrocenes out of the large number of possible examples have been prepared so far. The first part of this review summarizes the syntheses of all the homo- and heterohaloferrocenes known up to date. The second part summarizes typical reactions of haloferrocenes, namely lithiation followed by trapping with an electrophile, copper-mediated halogen substitution, coupling with formation of diferrocenyl derivatives, ortho-lithiation followed by trapping with an electrophile, palladium-catalyzed coupling reactions and finally miscellaneous reactions.1 Introduction2 Homohaloferrocenes2.1 Fluoroferrocenes2.2 Chloroferrocenes2.3 Bromoferrocenes2.4 Iodoferrocenes3 Heterohaloferrocenes4 Selected Reactions of Haloferrocenes4.1 Lithiation Followed by Trapping with an Electrophile4.2 Copper-Mediated Halogen Substitution4.3 Coupling with Formation of Diferrocenyl Derivatives4.4 ortho-Lithiation of Haloferrocenes4.5 Palladium-Catalyzed Reactions of Haloferrocenes4.6 Miscellaneous Reactions of Haloferrocenes5 Conclusions

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Palladium-catalyzed reaction of 2-iodoferrocenyl alcohols with internal alkynes: Synthesis of functionally 1,2-disubstituted ferrocenes and ferroceno-pyrans

Cited by 9 publications

References 106 publications

Synthesis, characterization and X-ray crystal structures of chiral ferrocene-containing β-diketones

Synthesis, characterization and X-ray crystal structures of chiral ferrocene-containing β-diketones

Bifunctional N‐Heterocyclic Carbene Ferrocenyl Ligands – Synthesis and Palladium(II) Complexes

Haloferrocenes: Syntheses and Selected Reactions

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