Synthesis, structure and reactivity of novel pyridazine-coordinated diiron bridging carbene complexes

Xiao, Nu; Xu, Qiang; Chen, Jiabi

doi:10.1039/b505141j

Cited by 12 publications

(7 citation statements)

References 26 publications

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“…Although similar reactivity is observed if 5 is exposed to an atmosphere of H 2 , the reaction does not proceed cleanly. Significant quantities of dissociated ligand are observed by 31 P NMR, implying that N 2 stabilizes one or more of the intermediates.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Activation of an Open Shell, Carbyne-Bridged Diiron Complex Toward Binding of Dinitrogen

Arnett

Agapie

2020

J. Am. Chem. Soc.

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Experimental and Synthetic Details General Considerations All reactions were performed at room temperature in a nitrogen filled M. Braun glovebox or using standard Schlenk techniques unless otherwise specified. Glassware was oven dried at 140 o C for at least two hours prior to use, and allowed to cool under vacuum. Bis(odiisopropylphosphinophenyl)-chlorophosphine (P2P Cl) was prepared as described elsewhere. 1 All other reagents were obtained commercially unless otherwise noted and typically stored over activated 4 Å molecular sieves. Tetrahydrofuran, toluene-d8 and benzene-d6 were dried using sodium/benzophenone ketyl, degassed with three freeze-pump-thaw cycles, vacuum transferred, and stored over 3 Å molecular sieves prior to use. Diethyl ether, benzene, toluene, acetonitrile, hexanes, and pentane were dried by sparging with nitrogen for at least 15 minutes, then passing through a column of activated A2 alumina under positive nitrogen pressure. 1 H and 31 P NMR spectra were recorded on a Varian 300 or 400 MHz spectrometer. All chemical shifts (δ) are reported in ppm, and coupling constants (J) are in hertz. The 1 H-NMR spectra were referenced using residual H impurity in the deuterated solvent. UV-Vis spectra were recorded on a Varian Cary Bio 50 spectrophotometer. Infrared (ATR-IR) spectra were recorded on a Bruker ALPHA ATR-IR spectrometer. Elemental analyses were performed at Caltech. Physical Methods Mössbauer Measurements. Zero field 57 Fe Mössbauer spectra were recorded in constant acceleration on a spectrometer from See Co (Edina, MN) equipped with an SVT-400 cryostat (Janis, Wilmington, WA). The quoted isomer shifts are relative to the centroid of the spectrum of α-Fe foil at room temperature. Unless otherwise noted, samples were prepared by grinding polycrystalline (20-50 mg) into a fine powder and pressed into a homogenous pellet with boron nitride in a cup fitted with a screw cap. The data were fitted to Lorentzian lineshapes using the program WMOSS (www.wmoss.org). Magnetic Measurements. Magnetic measurements for 5 were conducted with a Quantum Design MPMS3 SQUID Magnetometer at the University of California, Los Angeles. A polycrystalline sample of 5 was wrapped in plastic film and placed in a gelatin capsule. The capsule was then inserted into a plastic straw. Magnetization data at 100 K from 0 to 4 T were collected to confirm the absence of ferromagnetic impurities. Direct current variable temperature magnetic susceptibility measurements were collected between 1.8 and 300 K with a 0.1 T field. Magnetic susceptibility data was corrected for diamagnetism of the sample, estimated using Pascal's constants. Magnetic susceptibility data was simulated with PHI. 2 X-ray Crystallography. For compounds 4-8, low-temperature (100 K) diffraction data (φand ω-scans) were collected on a Bruker AXS D8 VENTURE KAPPA diffractometer coupled to a PHOTON 100 CMOS detector with Mo Kα radiation (λ = 0.71073 Å) or with Cu Kα (λ = 1.54178 Å). All diffractometer manipulations, including data collection, integration, and ...

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Section: ■ Results and Discussionmentioning

confidence: 99%

Activation of an Open Shell, Carbyne-Bridged Diiron Complex Toward Binding of Dinitrogen

Arnett

Agapie

2020

J. Am. Chem. Soc.

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“…The bridging alkoxycarbene complex 4 in ether was treated, similar to the procedures for the preparation of the COT-coordinated diiron cationic bridging carbyne complexes [Fe 2 (l-CAr)(CO) 4 (g 8 -C 8 H 8 )]BF 4 [11] and pyridazine-coordinated diiron cationic bridging carbyne complex [(C 4 H 4 N 2 )Fe 2 (l-CAr)(CO) 6 ]BF 4 [20] with an exess of HBF 4 AEEt 2 O at low temperature (À60 to À30°C) for 1 h to give a brown-red solid [Fe 2 (l-CC 6 H 4 CF 3 -p)(l-CO)(CO) 2 (g 5 -C 9 H 7 ) 2 ]BF 4 (5) (Eq. (2)) in 85% yield.…”

Section: Resultsmentioning

confidence: 99%

Syntheses, structures and reactivities of diindenyl-coordinated diiron bridging carbene complexes

Zhang

Zhu

et al. 2006

Journal of Organometallic Chemistry

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“…There is a variety of dinuclear complexes with pyridazine or phthalazine featuring Cu, 17 Fe, 18 Sn, 19 In, 20 In 2010 Wagner and co-workers demonstrated a powerful strategy to access boron-based polymers. The monomeric unit is based on 9,10-diboraanthracene 15 (Scheme 4).…”

Section: Interaction Of Bidentate Lewis Acids With 12-diazenesmentioning

confidence: 99%

“…15,16 This account summarizes our efforts and puts the results into perspective. There is a variety of dinuclear complexes with pyridazine or phthalazine featuring Cu, 17 Fe, 18 Sn, 19 In, 20 Rh 21 or Pt 22 as binding metal. Also, bidentate Lewis acids based on boron have been complexed with 1,2-diazenes.…”

Section: Introductionmentioning

confidence: 99%

Bidentate Lewis Acids as Catalysts for the Activation of 1,2-Diazenes in Organic Synthesis

Wegner¹,

Kessler²

2012

Synlett

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A new concept for the catalysis of the inverse-electrondemand Diels-Alder (IEDDA) reaction of 1,2-diazenes using bidentate Lewis acid was recently reported by our group. The general catalytic principle is based on the simultaneous coordination of the bidentate Lewis acid to the 1,2-diazene moiety, lowering the LUMO to facilitate the cycloaddition step. Extrusion of N 2 regenerates the catalyst and after elimination the aromatic product is obtained. In this account the development of this new catalytic principle is described and put into the general context of Lewis acid catalysis.

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Synthesis, structure and reactivity of novel pyridazine-coordinated diiron bridging carbene complexes

Cited by 12 publications

References 26 publications

Activation of an Open Shell, Carbyne-Bridged Diiron Complex Toward Binding of Dinitrogen

Activation of an Open Shell, Carbyne-Bridged Diiron Complex Toward Binding of Dinitrogen

Syntheses, structures and reactivities of diindenyl-coordinated diiron bridging carbene complexes

Bidentate Lewis Acids as Catalysts for the Activation of 1,2-Diazenes in Organic Synthesis

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