Synthesis and reactivity of an unprecedented osmium(VIII) alkylidene

Martin, Véronique I.; Blakey, Simon B.

doi:10.1016/j.tetlet.2008.09.064

Cited by 5 publications

(2 citation statements)

References 34 publications

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“…After filtration, the solvent was removed completely under vacuum. Products 5 , 6 − 8 , 9 , 10 , 11 , 12 , 13 , 15 , 16 , 17 − 22 , 23 − 26 , and 27 − 28 were indentified by comparison of NMR data with those in the literature; yields and regioselectivity were determined by integration ratio using 1,3,5-trimethoxylbenzene as internal standard or after purification with column chromatography on silica gel.…”

Section: Methodsmentioning

confidence: 99%

Efficient Heck Reactions Catalyzed by Palladium(0) and -(II) Complexes Bearing N-Heterocyclic Carbene and Amide Functionalities

et al. 2010

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A palladium(0) NHC complex Pd0(LH1)2(MA) (MA = maleic anhydride) was prepared from the amide-imidazolium salt [LH1H2]Cl (H1 = NH proton; H2 NCHN proton). The X-ray diffraction studies confirmed that a η2-MA ligand and two monodentate NHC ligands with the H1 protons remaining intact are coordinated. These NH protons are involved in intra- or intermolecular hydrogen bonds stabilizing the solid-state structure. Degradation of Pd(LH1)2(MA) in air leads to the formation of the chelate complex trans-PdIIL2 and other unidentified products. Negative-ion electrospray mass spectrometry revealed some intriguing Pd(0) species, including a 14-electron [Pd0L]− species that bears only a bidentate NHC/amido ligand. The anionic amido group imparts a high electron density on a palladium center, as shown by X-ray photoelectron study. The palladium(0) precatalyst is highly efficient in catalyzing Heck reactions with activated aryl chlorides in ionic liquid. For deactivating aryl chlorides and bulky aryl bromides, cis-PdIIL2 is more effective. A range of Heck-coupled products can be prepared by Pd0(LH1)2(MA) and cis-PdIIL2. The latter complex also successfully mediates one-pot sequential Heck/Heck and Suzuki/Heck coupling reactions with 4-bromochlorobenzene as substrate.

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Section: Methodsmentioning

confidence: 99%

Efficient Heck Reactions Catalyzed by Palladium(0) and -(II) Complexes Bearing N-Heterocyclic Carbene and Amide Functionalities

et al. 2010

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“…After filtration, the solvent was removed completely under vacuum. Products 6 , 7 − 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 − 21 , 22 , 23 and 24 , 25 and 26 , and 27 − 30 66 were identified by comparison of their NMR data with those in the literature; NMR yields and regioselectivity were determined by integration ratio using 1,3,5-trimethoxylbenzene as internal standard. Isolated yields were obtained after purification with column chromatography on silica gel.…”

Section: Methodsmentioning

confidence: 99%

A Heteroleptic Palladium(II) Complex Containing a Bidentate Carbene/Amido Ligand and 3-(Trifluoromethyl)-5-(2-pyridyl)pyrazolate: Fast Catalyst Activation in the Heck Coupling Reaction

et al. 2010

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A multicomponent reaction between PdCl 2 , fppzH, and [LH 1 H 2 ]Cl in the presence of K 2 CO 3 (L= bidentate amido/carbene; fppzH = 3-(trifluoromethyl)-5-(2-pyridyl)pyrazole) allows the preparation of PdL(fppz) in good yield. The analogous platinum complex, however, needs to be prepared by a twostep procedure. The new palladium(II) and platinum(II) complexes were characterized by 1D and 2D NMR spectroscopy, X-ray crystallography, electrospray ionization mass spectrometry, and elemental analyses. X-ray photoelectron spectroscopy indicates the high electron richness of the palladium atoms in PdL(fppz). These palladium complexes are efficient in catalyzing Heck coupling reactions with challenging aryl halide substrates. The catalyst activation in PdL(fppz) is significantly faster than that in cis-PdL 2 . A mere 0.5 mol % of palladium loading is enough to afford a 82% yield of coupled product from 4-chloroanisole and styrene in 24 h.

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Metal-Carbon Bonds of Heavier Group 7 and 8 Metals (Tc, Re, Ru, Os): Mononuclear Tc/Re/Ru/Os Complexes With Metal-Carbon Bonds

Wei

Jia

2021

Comprehensive Coordination Chemistry III

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Synthesis and reactivity of an unprecedented osmium(VIII) alkylidene

Cited by 5 publications

References 34 publications

Efficient Heck Reactions Catalyzed by Palladium(0) and -(II) Complexes Bearing N-Heterocyclic Carbene and Amide Functionalities

Efficient Heck Reactions Catalyzed by Palladium(0) and -(II) Complexes Bearing N-Heterocyclic Carbene and Amide Functionalities

A Heteroleptic Palladium(II) Complex Containing a Bidentate Carbene/Amido Ligand and 3-(Trifluoromethyl)-5-(2-pyridyl)pyrazolate: Fast Catalyst Activation in the Heck Coupling Reaction

Metal-Carbon Bonds of Heavier Group 7 and 8 Metals (Tc, Re, Ru, Os): Mononuclear Tc/Re/Ru/Os Complexes With Metal-Carbon Bonds

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