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Meyer, Karsten

Publications and source records attributed to Meyer, Karsten.

C sp 2 –H/F bond activation and borylation with iron

Reduction of [K 2 {( tBu pyrr 2 pyr)Fe} 2 (μ-N 2 )] (1) with two equiv. of KC 8 in the presence of crown-ether 18-C-6 yields the N 2 adduct [{K(18-C-6)} 2 ( tBu pyrr 2 pyr)Fe(N 2 )] (2). Complex 2 heterolytically splits the C sp 2 –H bond of benzene to form [{K(18-C-6)}( tBu pyrr 2 pyr)Fe(C 6 H 5 )] (3), whereby usage of a diboron B 2 pin 2 promotes hydride elimination to form the salt [K(18-C-6)HB 2 Pin 2 ] (4). Similarly, 3 can also be formed by cleavage of the C–F bond of fluorobenzene. Reaction of 3 with ClBcat yields [K(18-C-6)(thf) 2 ][( tBu pyrr 2 pyr)FeCl] (5) and PhBcat and the former can be reduced to 2 to complete a synthetic cycle for heterolytic benzene C–H activation and borylation.

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Divalent Titanium via Reductive N−C Coupling of a Ti IV Nitrido with π ‐Acids

The nitrido-ate complex [(PN) 2 Ti(N){μ 2 -K(OEt 2 )}] 2 (1) (PN − =(N-(2-P i Pr 2 -4-methylphenyl)-2,4,6-Me 3 C 6 H 2 ) reductively couples CO and isocyanides in the presence of DME or cryptand (Kryptofix222), to form rare, five-coordinate Ti II complexes having a linear cumulene motif, [K(L)][(PN) 2 Ti(NCE)] (E=O, L=Kryptofix222, (2); E=NAd, L=3 DME, (3); E=N t Bu, L=3 DME, (4); E=NAd, L=Kryptofix222, (5)). Oxidation of 2–5 with [Fc][OTf] afforded an isostructural Ti III center containing a neutral cumulene, [(PN) 2 Ti(NCE)] (E=O, (6); E=NAd (7), N t Bu (8)) and characterization by CW X-band EPR spectroscopy, revealed unpaired electron to be metal centric. Moreover, 1e − reduction of 6 and 7 in the presence of Kryptofix222cleanly reformed corresponding discrete Ti II complexes 2 and 5, which were further characterized by solution magnetization measurements and high-frequency and -field EPR (HFEPR) spectroscopy. Furthermore, oxidation of 7 with [Fc*][B(C 6 F 5 ) 4 ] resulted in a ligand disproportionated Ti IV complex having transoid carbodiimides, [(PN) 2 Ti(NCNAd) 2 ] (9). Comparison of spectroscopic, structural, and computational data for the divalent, trivalent, and tetravalent systems, including their 15 N enriched isotopomers demonstrate these cumulenes to decrease in order of backbonding as Ti II →Ti III →Ti IV and increasing order of π-donation as Ti II →Ti III →Ti IV , thus displaying more covalency in Ti III species. Lastly, we show a synthetic cycle whereby complex 1 can deliver an N-atom to CO and CNAd.

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Iron‐Catalyzed Intermolecular C−H Amination Assisted by an Isolated Iron‐Imido Radical Intermediate

Here we report the use of a base metal complex [( tBu pyrpyrr 2 )Fe(OEt 2 )] (1-OEt 2 ) ( tBu pyrpyrr 2 2− =3,5-tBu 2 -bis(pyrrolyl)pyridine) as a catalyst for intermolecular amination of C sp3 −H bonds of 9,10-dihydroanthracene (2 a) using 2,4,6-trimethyl phenyl azide (3 a) as the nitrene source. The reaction is complete within one hour at 80 °C using as low as 2 mol % 1-OEt 2 with control in selectivity for single C−H amination versus double C−H amination. Catalytic C−H amination reactions can be extended to other substrates such as cyclohexadiene and xanthene derivatives and can tolerate a variety of aryl azides having methyl groups in both ortho positions. Under stoichiometric conditions the imido radical species [( tBu pyrpyrr 2 )Fe{=N(2,6-Me 2 -4-tBu-C 6 H 2 )] (1-imido) can be isolated in 56 % yield, and spectroscopic, magnetometric, and computational studies confirmed it to be an S = 1 Fe IV complex. Complex 1-imido reacts with 2 a to produce the ferrous aniline adduct [( tBu pyrpyrr 2 )Fe{NH(2,6-Me 2 -4-tBu-C 6 H 2 )(C 14 H 11 )}] (1-aniline) in 45 % yield. Lastly, it was found that complexes 1-imido and 1-aniline are both competent intermediates in catalytic intermolecular C−H amination.

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Isostructural bridging diferrous chalcogenide cores [Fe II (μ-E)Fe II ] (E = O, S, Se, Te) with decreasing antiferromagnetic coupling down the chalcogenide series

Iron compounds containing a bridging oxo or sulfido moiety are ubiquitous in biological systems, but substitution with the heavier chalcogenides selenium and tellurium, however, is much rarer, with only a few examples reported to date. Here we show that treatment of the ferrous starting material [( tBu pyrpyrr 2 )Fe(OEt 2 )] (1-OEt 2 ) ( tBu pyrpyrr 2 = 3,5- t Bu 2 -bis(pyrrolyl)pyridine) with phosphine chalcogenide reagents E = PR 3 results in the neutral phosphine chalcogenide adduct series [( tBu pyrpyrr 2 )Fe(EPR 3 )] (E = O, S, Se; R = Ph; E = Te; R = t Bu) (1-E) without any electron transfer, whereas treatment of the anionic starting material [K] 2 [( tBu pyrpyrr 2 )Fe 2 (μ-N 2 )] (2-N 2 ) with the appropriate chalcogenide transfer source yields cleanly the isostructural ferrous bridging mono-chalcogenide ate complexes [K] 2 [( tBu pyrpyrr 2 )Fe 2 (μ-E)] (2-E) (E = O, S, Se, and Te) having significant deviation in the Fe–E–Fe bridge from linear in the case of E = O to more acute for the heaviest chalcogenide. All bridging chalcogenide complexes were analyzed using a variety of spectroscopic techniques, including 1 H NMR, UV-Vis electronic absorbtion, and 57 Fe Mössbauer. The spin-state and degree of communication between the two ferrous ions were probed via SQUID magnetometry, where it was found that all iron centers were high-spin (S = 2) Fe II , with magnetic exchange coupling between the Fe II ions. Magnetic studies established that antiferromagnetic coupling between the ferrous ions decreases as the identity of the chalcogen is tuned from O to the heaviest congener Te.

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Uranium-Mediated Peroxide Activation and a Precursor toward an Elusive Uranium cis -Dioxo Fleeting Intermediate

The activation of chalcogen–chalcogen bonds using organometallic uranium complexes has been well documented for S–S, Se–Se, and Te–Te bonds. In stark contrast, reports concerning the ability of a uranium complex to activate the O–O bond of an organic peroxide are exceedingly rare. Herein, we describe the peroxide O–O bond cleavage of 9,10-diphenylanthracene-9,10-endoperoxide in nonaqueous media, mediated by a uranium(III) precursor [(( Me,Ad ArO) 3 N)U III (dme)] to generate a stable uranium(V) bis-alkoxide complex, namely, [(( Me,Ad ArO) 3 N)U V (DPAP)]. This reaction proceeds via an isolable, alkoxide-bridged diuranium(IV/IV) species, implying that the oxidative addition occurs in two sequential, single-electron oxidations of the metal center, including rebound of a terminal oxygen radical. Furthermore, this uranium(V) bis-alkoxide can then be reduced with KC 8 to form a uranium(IV) complex, which upon exposure to UV light, in solution, releases 9,10-diphenylanthracene to generate a cyclic uranyl trimer through formal two-electron photooxidation. Analysis of the mechanism of this photochemical oxidation via density functional theory (DFT) calculations indicates that the formation of this uranyl trimer occurs through a fleeting uranium cis-dioxo intermediate. At room temperature, this cis-configured dioxo species rapidly isomerizes to a more stable trans configuration through the release of one of the alkoxide ligands from the complex, which then goes on to form the isolated uranyl trimer complex.

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Tale of Three Molecular Nitrides: Mononuclear Vanadium (V) and (IV) Nitrides As Well As a Mixed-Valence Trivanadium Nitride Having a V 3 N 4 Double-Diamond Core

Here, transmetallation of [VCl 3 (THF) 3 ] and [TlTp tBu,Me ] afforded [(Tp tBu,Me )VCl 2 ] (1, Tp tBu,Me = hydro-tris(3-tert-butyl-5-methylpyrazol-1-yl)borate), which was reduced with KC 8 to form a $C_{3v}$ symmetric V II complex, [(Tp tBu,Me )VCl] (2). Complex 1 has a high-spin ($\textit{S}$ = 1) ground state and displays rhombic high-frequency and -field electron paramagnetic resonance (HFEPR) spectra, while complex 2 has an $\textit{S}$ = 3/2 4 A 2 ground state observable by conventional EPR spectroscopy. Complex 1 reacts with NaN 3 to form the V V nitride-azide complex [(Tp tBu,Me )V≡N(N 3 )] (3). A likely V III azide intermediate en route to 3, [(Tp tBu,Me )VCl(N 3 )] (4), was isolated by reacting 1 with N 3 SiMe 3 . Complex 4 is thermally stable but reacts with NaN3 to form 3, implying a bis-azide intermediate, [(Tp tBu,Me )V(N 3 ) 2 ] (A), leading to 3. Reduction of 3 with KC 8 furnishes a trinuclear and mixed-valent nitride, [{(Tp tBu,Me )V} 2 ($μ_{4-}$VN 4 )] (5), conforming to a Robin–Day class I description. Complex 5 features a central vanadium ion supported only by bridging nitride ligands. Contrary to 1, complex 2 reacts with NaN 3 to produce an azide-bridged dimer, [{(Tp tBu,Me )V} 2 (1,3-$μ_2$-N 3 ) 2 ] (6), with two antiferromagnetically coupled high-spin V II ions. Complex 5 could be independently produced along with [($κ_2$-Tp tBu,Me ) 2 V] upon photolysis of 6 in arene solvents. The putative {V IV ≡N} intermediate, [(Tp tBu,Me )V≡N] (B), was intercepted by photolyzing 6 in a coordinating solvent, such as tetrahydrofuran (THF), yielding [(Tp tBu,Me )V≡N(THF)] (B-THF). In arene solvents, B-THF expels THF to afford 5 and [($κ_2$-Tp tBu,Me ) 2 V]. A more stable adduct (B-OPPh 3 ) was prepared by reacting B-THF with OPPh 3 . These adducts of B are the first neutral and mononuclear V IV nitride complexes to be isolated.

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