<i>C</i>‐Bridged Bispyrrolidines and Bispiperidines as New Ligands

Stumpf, Tim‐Daniel J.; Steinbach, Manfred; Höltke, Magdalena; Heuger, Gerold; Grasemann, Franka; Fröhlich, Roland; Schindler, Siegfried; Göttlich, Richard

doi:10.1002/ejoc.201801075

Cited by 7 publications

(7 citation statements)

References 37 publications

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“…The synthesis of the ligand bis(2‐piperidinyl)methane (BP; Scheme : n = 2, R 1 = R 2 = R 3 = H; rac and meso ) is described elsewhere . BP was obtained and used as a bidentate ligand in both diastereomeric forms.…”

Section: Resultsmentioning

confidence: 99%

“…The solvents were purified by distillation and dried by standard procedures or used from an SPS‐800 solvent purification system by MBraun (Garching, Germany). The syntheses of the BP and BQ ligands are reported elsewhere . Preparations under anaerobic conditions were performed in Schlenk tubes under dry nitrogen or in an MBraun glovebox under argon.…”

Section: Methodsmentioning

confidence: 99%

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Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands

et al. 2017

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Copper complexes with bis(piperidinyl)methane (BP) and bis(quinolinyl)methane (BQ) ligands were investigated. A dinuclear carbonato-bridged copper(II) complex as well as a dinuclear copper(I) complex with BP ligands were structurally characterized. The reaction of a copper(I)-BP complex was investigated by low-temperature stopped-flow techniques, which showed that the very fast formation of a bis(μ-oxido)copper intermediate leads to an intramolecular ligand hydroxylation.[a]

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands

et al. 2017

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“…The NP designation indicates that the arene group is a naphthyl moiety. Also, we chose a non-capping arene ligand (dpe, 1,2-di-2-pyridylethane, complexes labeled with 5 ) to compare the formation of Me–X for Rh III complexes with a similar bis-pyridyl ligand motif that lacks the capping arene feature. , The pro-ligand 6-FP ( 2 ) was synthesized by a palladium-catalyzed Suzuki coupling reaction using 8-quinolylboronic acid and 1,2-diiodobenzene as the starting materials (Scheme ), and 6- NP FP ( 4 ) was synthesized using a similar method but with Cs 2 CO 3 as the base and without the use of water. , Most peaks in the 1 H NMR spectrum of 6-FP are broadened (Figure S7), which is likely due to the hindered rotation of the C–C bond connecting the arene and quinoline moieties. The compound 5- NP FP ( 3 ) was synthesized using a procedure similar to that used for 5-FP …”

Section: Resultsmentioning

confidence: 99%

“…All spectra were recorded at 25 °C unless otherwise indicated. Literature procedures were used to prepare 5-FP ( 1 ), dpe ( 5 ), and [Rh(η 2 -C 2 H 4 ) 2 (μ-Cl)] 2 . ,, …”

Section: Methodsmentioning

confidence: 99%

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Functionalization of Rh^III–Me Bonds: Use of “Capping Arene” Ligands to Facilitate Me–X Reductive Elimination

Chen

Musgrave

et al. 2021

Organometallics

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We show how to improve the yield of MeX from CH 4 activation catalysts from 12% to 90% through the use of "capping arene" ligands. Four (FP)Rh III (Me)(TFA) 2 {FP = "capping arene" ligands, including 8,8′-(1,2-phenylene)diquinoline (6-FP), 8,8′-(1,2naphthalene)diquinoline (6-NP FP), 1,2-bis(N-7-azaindolyl)benzene (5-FP), and 1,2-bis(N-7-azaindolyl)naphthalene (5-NP FP)} complexes. These complexes and (dpe)Rh III (Me)(TFA) 2 (dpe = 1,2-di-2-pyridylethane) were synthesized and tested for their performance in reductive elimination of MeX (X = TFA or halide). The FP ligands were used with the goal of blocking a coordination site to destabilize the Rh III complexes and facilitate MeX reductive elimination. On the basis of single-crystal X-ray diffraction studies, the 6-FP and 6-NP FP ligated Rh complexes have Rh−arene distances shorter than those of the 5-FP and 5-NP FP Rh complexes; thus, it is expected that the Rh−arene interactions are weaker for the 5-FP complexes than for the 6-FP complexes. Consistent with our hypothesis, the 5-FP and 5-NP FP Rh III complexes demonstrate improved performance (from 12% to ∼60% yield) in the reductive elimination of MeX. The reductive elimination of MeX from (FP)Rh III (Me)(TFA) 2 can be further improved by the use of chemical oxidants. For example, the addition of 2 equiv of AgOTf leads to 87(2)% yield of MeTFA and can be achieved in CD 3 CN at 90 °C using (5-FP)Rh(Me)(TFA) 2 .

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Substitution Effects on the Photophysical and Photoredox Properties of Tetraaza[7]helicenes

Rocker,

Dresel,

Krieger

et al. 2023

Chemistry A European J

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A series of substituted derivatives of tetraaza [7]helicenes were synthesized and the influence of the substitution on their photophysical and photoredoxcatalytic properties was studied. The combination of their high fluorescence quantum yields of up to 0.65 and their circularly polarized luminescence (CPL) activity results in CPL brightness values (B CPL ) that are among the highest recorded for [7]helicenes so far. A sulfonylation/hetarylation reaction using cyanopyridines as substrates for photoinduced electron transfer (PET) from the excited helicenes was conducted to test for viability in photoredox catalysis. DFT calculations predict the introduction of electron withdrawing substituents to yield more oxidizing catalysts.

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C‐Bridged Bispyrrolidines and Bispiperidines as New Ligands

Cited by 7 publications

References 37 publications

Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands

Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands

Functionalization of Rh^III–Me Bonds: Use of “Capping Arene” Ligands to Facilitate Me–X Reductive Elimination

Substitution Effects on the Photophysical and Photoredox Properties of Tetraaza[7]helicenes

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C‐Bridged Bispyrrolidines and Bispiperidines as New Ligands

Cited by 7 publications

References 37 publications

Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands

Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands

Functionalization of RhIII–Me Bonds: Use of “Capping Arene” Ligands to Facilitate Me–X Reductive Elimination

Substitution Effects on the Photophysical and Photoredox Properties of Tetraaza[7]helicenes

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Functionalization of Rh^III–Me Bonds: Use of “Capping Arene” Ligands to Facilitate Me–X Reductive Elimination