Oxidative Addition von 2‐Halogenazolen – direkte Synthese von Palladium(II)‐Komplexen mit protischen NH,NH‐funktionalisierten NHC‐Liganden

Das, Rajorshi; Daniliuc, Constantin G.; Hahn, F. Ekkehardt

doi:10.1002/ange.201308269

Cited by 13 publications

(1 citation statement)

References 71 publications

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“…This synthetic methodology provided a pathway to generate a wide range of heterocyclic carbene metal complexes. ,– Depending on whether an amine or an alcohol was featured as a nucleophile, this approach led to NH,NH– or NH,O–NHC–metal complexes via the 1,2 addition of the nucleophile onto the isonitrile triple bond. These complexes could be functionalized by alkylation of the free NH moiety (Scheme a). – Furthermore, Fehlhammer et al used coordinated isonitriles bearing an activated methylene group attached to a second electron-withdrawing group. These precursor complexes were able to react with aldehydes, nitriles, isocyanates, thioisocyanates, ketenimines, and carbon disulfide as dipolarophiles in a [3 + 2]-cycloaddition toward the corresponding pNHC–metal complexes (Scheme b).…”

Section: Introductionmentioning

confidence: 99%

Modular Approach toward Protic N-Heterocyclic Carbene Complexes from Tosylated Benzyl Isocyanide Metal Complexes and Imines

Hubbert,

Dietl,

Zahner

et al. 2023

Organometallics

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Tosylated benzyl isocyanide complexes of gold(I), iridium(III), ruthenium(II), and rhodium(III) precursors were prepared and converted to the corresponding protic N-heterocyclic carbene (pNHC) metal complexes by reacting with imines. This modular approach offers a straightforward strategy for synthesizing pNHC−metal complexes starting from readily available imine precursors. In contrast to the common disconnection of isonitrile-based NHC complexes, which are synthesized by the addition of amines with tethered electrophiles, this approach also gives access to pNHC complexes of other catalytically relevant metals like ruthenium, rhodium, and iridium.

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Section: Introductionmentioning

confidence: 99%

Modular Approach toward Protic N-Heterocyclic Carbene Complexes from Tosylated Benzyl Isocyanide Metal Complexes and Imines

Hubbert,

Dietl,

Zahner

et al. 2023

Organometallics

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Synthese von Komplexen mit anomalen “protischen” N‐heterocyclischen Carbenen

2015

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Neutrales 4-Iod-N-ethylimidazol (3)k ann oxidativ an [Pt(PPh 3 ) 4 ]a ddiert werden, wobei in Gegenwart von Tetraalkylammoniumsalzen die Komplexe trans-[4], trans-[5] und trans-[6]g ebildet werden, die einen anionischen,a mC 4-Atom gebundenen Heterocyclus mit einem unsubstituierten Ring-Stickstoffatom enthalten. Der Komplex trans-[4]reagiert mit der Protonenquelle NH 4 Iu nter Protonierung des Ring-Stickstoffatoms und Bildung des Komplexes trans-[7]I, der einen NH,NR-substituierten aNHC-Liganden trägt. Die Reaktion von trans-[4]m it CH 3 If ührt zum Komplex trans-[8]I mit einem klassischen aNHC-Liganden mit zwei alkylierten Ring-Stickstoffatomen.

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Preparation of Complexes Bearing N‐Alkylated, Anionic or Protic CAACs Through Oxidative Addition of 2‐Halogenoindole Derivatives

et al. 2020

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CAAC precursors 2‐chloro‐3,3‐dimethylindole 1 and 2‐chloro‐1‐ethyl‐3,3‐dimethylindolium tetrafluoroborate 2BF4 have been prepared and oxidatively added to [M(PPh3)4] (M=Pd, Pt). Salt 2BF4 reacts with [Pd(PPh3)4] in toluene at 25 °C over 4 days to yield complex cis‐[3]BF4 featuring an N‐ethyl substituted CAAC, two cis‐arranged phosphines and a chloro ligand. Compound trans‐[3]BF4 was obtained from the same reaction at 80 °C over 1 day. Salt 2BF4 reacts with [Pt(PPh3)4] to give cis‐[4]BF4. The neutral indole derivative 1 adds oxidatively to [Pt(PPh3)4] to give trans‐[5] featuring a CAAC ligand with an unsubstituted ring‐nitrogen atom. This nitrogen atom has been protonated with py⋅HBF4 to give trans‐[6]BF4 bearing a protic CAAC ligand. The PdII complex trans‐[7]BF4 bearing a protic CAAC ligand was obtained in a one‐pot reaction from 1 and [Pd(PPh3)4] in the presence of py⋅HBF4.

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Oxidative Addition von 2‐Halogenazolen – direkte Synthese von Palladium(II)‐Komplexen mit protischen NH,NH‐funktionalisierten NHC‐Liganden

Cited by 13 publications

References 71 publications

Modular Approach toward Protic N-Heterocyclic Carbene Complexes from Tosylated Benzyl Isocyanide Metal Complexes and Imines

Modular Approach toward Protic N-Heterocyclic Carbene Complexes from Tosylated Benzyl Isocyanide Metal Complexes and Imines

Synthese von Komplexen mit anomalen “protischen” N‐heterocyclischen Carbenen

Preparation of Complexes Bearing N‐Alkylated, Anionic or Protic CAACs Through Oxidative Addition of 2‐Halogenoindole Derivatives

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