Nội dung được dịch bởi AI, chỉ mang tính chất tham khảo
Phản ứng kết hợp Fe–C xúc tác bằng kim loại chuyển tiếp trong tổng hợp phức chất dicarbonyl(2-thienylethynyl)(η5-cyclopentadienyl)iron: Nghiên cứu quang phổ, cấu trúc và điện hóa
Tóm tắt
Phức chất σ-alkynyl sắt(II) mới Cp(CO)2Fe-C≡C-(2-C4H3S) đã được tổng hợp bằng cách áp dụng một số phương pháp đã biết dựa trên các phản ứng kết hợp Fe–C xúc tác bởi kim loại chuyển tiếp (Pd/Cu–, Au–, Cu– và Pd–) giữa 2-ethynylthiophen hoặc 2-[(trimethylsilyl)ethynyl]thiophen với iodide cyclopentadienyliron dicarbonyl. Năng suất của phức chất trong các phản ứng này được phát hiện là phụ thuộc mạnh vào xúc tác được sử dụng. Các điều kiện, xúc tác và tá dược cung cấp năng suất cao nhất cho phức chất 2-thienylethynyl sắt mong muốn đã được xác định. Phức chất được đặc trưng bằng phổ IR, 1H và 13C NMR. Cấu trúc phân tử của Cp(CO)2Fe–C≡C-(2-C4H3S) được xác định bởi phân tích nhiễu xạ tia X cho thấy cấu hình hình học ghế ba chân. Tính chất oxy hóa khử của phức chất mới được nghiên cứu.
Từ khóa
#Fe–C coupling #σ-alkynyl iron(II) complex #transition metal catalysis #spectroscopy #electrochemical propertiesTài liệu tham khảo
Low PJ (2013) Twists and turns: Studies of the complexes and properties of bimetallic complexes featuring phenylene ethynylene and related bridging ligands. Coord Chem Rev 257:1507–1532. https://doi.org/10.1016/j.ccr.2012.08.008
Grelaud G, Cifuentes MP, Paul F, Humphrey MG (2014) Group 8 metal alkynyl complexes for nonlinear optics. J Organomet Chem 751:181–200. https://doi.org/10.1016/j.jorganchem.2013.10.008
Yam VW-W, Au VK-M, Leung SY-L (2015) Light-emitting self-assembled materials based on d 8 and d 10 transition metal complexes. Chem Rev 115:7589–7728. https://doi.org/10.1021/acs.chemrev.5b00074
Li Y-P, Fan X-X, Wu Y et al (2017) High-efficiency organic light-emitting diodes of phosphorescent PtAg2 heterotrinuclear acetylide complexes supported by triphosphine. J Mater Chem C 5:3072–3078. https://doi.org/10.1039/C7TC00382J
Nakaya R, Yasuda S, Yorimitsu H, Oshima K (2011) (1-Alkynyl)dicarbonylcyclopentadienyliron complexes as electron-rich alkynes in organic synthesis: BF3-mediated [2+2] cycloaddition/ring-opening providing (2-alkenyl-1-imino)iron complexes. Chem - A Eur J 17:8559–8561. https://doi.org/10.1002/chem.201100669
Akita M, Koike T (2008) Chemistry of polycarbon species: from clusters to molecular devices. Dalt Trans 9226:3523–3530. https://doi.org/10.1039/b802069h
Valyaev DA, Peterleitner MG, Semeikin OV et al (2007) Proton reduction catalysis by manganese vinylidene and allenylidene complexes. J Organomet Chem 692:3207–3211. https://doi.org/10.1016/j.jorganchem.2007.01.055
Kaim V, Kaur-Ghumaan S (2019) Manganese complexes: hydrogen generation and oxidation. Eur J Inorg Chem 2019:5041–5051. https://doi.org/10.1002/ejic.201900988
Long NJ, Williams CK (2003) Metal alkynyl σ complexes: synthesis and materials. Angew Chemie - Int Ed 42:2586–2617. https://doi.org/10.1002/anie.200200537
Lo Sterzo C (1999) The wonder of palladium catalysis: from carbon–carbon to metal–carbon bond formation. An opportunity of getting astonishment from reality. Synlett 1999:1704–1722. https://doi.org/10.1055/s-1999-2919
Nakaya R, Yasuda S, Yorimitsu H, Oshima K (2009) Synthesis of (1-alkynyl)dicarbonylcyclopentadienyliron complexes by palladium-catalyzed Sonogashira-type carbon-iron bond formation. Tetrahedron Lett 50:5274–5276. https://doi.org/10.1016/j.tetlet.2009.07.005
Bruce MI, Ke M, Low PJ (1996) Syntheses of metal diynyl complexes: novel routes to all-carbon ligands. Chem Commun 3:2405–2406. https://doi.org/10.1039/cc9960002405
Osakada K, Yamamoto T (2000) Transmetallation of alkynyl and aryl complexes of group 10 transition metals. Coord Chem Rev 198:379–399. https://doi.org/10.1016/S0010-8545(99)00210-6
Bruce MI, Ke M, Low PJ et al (1998) Syntheses and chemistry of the diynyl complexes M(C≡CC≡CH)(CO)3(η-C5H5) (M = Mo, W): crystal structures of W(C≡CC≡CSiMe3)(CO)3(η-C5H5), W{C≡CC[CH=C(CN)2]=C(CN)2}(CO)3(η-C5H5), and cis-W(C≡CPh)(CO)2(PPh3)(η-C5H5). Organometallics 17:3539–3549. https://doi.org/10.1021/om980031r
Hashmi ASK, Molinari L (2011) Effective transmetalation from gold to iron or ruthenium. Organometallics 30:3457–3460. https://doi.org/10.1021/om200360q
Hiyama T (2002) How i came across the silicon-based cross-coupling reaction. J Organomet Chem 653:58–61. https://doi.org/10.1016/S0022-328X(02)01157-9
Crescenzi R, Lo Sterzo C (1992) Synthesis of metal acetylides via palladium-catalyzed carbon–metal bond formation. Organometallics 11:4301–4305. https://doi.org/10.1021/om00060a056
Pilar Gamasa M, Gimeno J, Lastra E et al (1991) Synthesis and characterization of novel σ-alkynyl cyclopentadienyl iron(II) complexes [Fe(C≡CR)L2(η-C5H5)] [L=CO; L2=bis(diphenylphosphino)methane (dppm)]. Crystal structure of [Fe(C≡CC6H5)(dppm)(η-C5H5)]. J Organomet Chem 405:333–345. https://doi.org/10.1016/0022-328X(91)86292-X
Akita M, Terada M, Oyama S, Morooka Y (1990) Preparation, structure, and divergent fluxional behavior of cationic dinuclear iron acetylides [Fp*2(C≡CR)]BF4 (R=H, Ph). Organometallics 9:816–825. https://doi.org/10.1021/om00117a043
Goddard R, Howard J, Woodward P (1974) Crystal and molecular structure of 1-(dicarbonyl-π-cyclopentadienylferrio)-2-(phenyl)-ethyne. J Chem Soc, Dalt Trans. https://doi.org/10.1039/DT9740002025
Steiner T, Tamm M (1998) Weak hydrogen bonds from Cp donors to C≡C acceptors. J Organomet Chem 570:235–239. https://doi.org/10.1016/S0022-328X(98)00867-5
Aechter B, Polborn K, Weinrich V, Beck W (1999) p-Tolyl(trimethylsilylethynyl)sulfone as synthon for the synthesis of Cp(OC)2M-C≡CSiMe3 (M = Fe, Ru). Molecular Structure of Cp(OC)2Fe-C≡CSiMe3. Zeitschrift für Naturforsch B 54:701–704. https://doi.org/10.1515/znb-1999-0521
Roué S, Le Stang S, Toupet L, Lapinte C (2003) Magnetic communication between two [(η5-C5Me5)(η2-dppe)Fe(III)] units mediated by the 2,5-bis(ethynyl)thiophene spacer. Comptes Rendus Chim 6:353–366. https://doi.org/10.1016/S1631-0748(03)00051-1
Bock S, Al-Owaedi OA, Eaves SG et al (2017) Single-molecule conductance studies of organometallic complexes bearing 3-thienyl contacting groups. Chem - A Eur J 23:2133–2143. https://doi.org/10.1002/chem.201604565
Mrózek O, Melounková L, Dostál L et al (2019) Enhanced cytotoxicity of indenyl molybdenum(ii) compounds bearing a thiophene function. Dalt Trans 48:11361–11373. https://doi.org/10.1039/C9DT01698H
Verpekin VV, Burmakina GV, Zimonin DV et al (2017) Electrochemical Study of a Heterobinuclear pyridylvinylidene complex Cp(CO)2Fe[μ-C=CH(2–C5H4N)]PdI. J Sib Fed Univ Chem 10:428–436. https://doi.org/10.17516/1998-2836-0038
Sahnoune H, Mahias V, Halet J-F, Lapinte C (2019) 1,4-Dimethoxybutadienediyl-bridged diiron compounds in three oxidation states: evaluation of delocalization effects. Organometallics 38:2724–2737. https://doi.org/10.1021/acs.organomet.9b00174
Anderson GK, Lin M, Sen A, Gretz E (1990) Bis(Benzonitrile)dichloro complexes of palladium and platinum. In: Angelici RJ (ed) Inorganic synthesis, vol 28. Wiley, New Jersey, pp 60–63
King RB, Stone FGA, Jolly WL et al (1963) Cyclopentadienyl metal carbonyls and some derivatives. In: Kleinberg J (ed) Inorganic syntheses, vol 7. John Wiley & Sons, Ltd, New Jersey, pp 99–115
Braunstein P, Lehner H, Matt D et al (1990) Platinum-gold cluster: chloro-1κCl-Bis(Triethylphosphine-1κP)Bis(Triphenylphosphine)-2κP, 3κP-Triangulo-Digold-Platinum(1+) Trifluoromethanesulfonate. In: Ginsberg AP (ed) Inorganic syntheses, vol 27. Wiley, New Jersey, pp 218–221
Weingand V, Wurm T, Vethacke V et al (2018) Intermolecular desymmetrizing gold-catalyzed Yne–Yne reaction of push-pull diarylalkynes. Chem - A Eur J 24:3725–3728. https://doi.org/10.1002/chem.201800360