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A kind of chiral nitrogen heterocyclic carbene precursor compound with benzimidazole skeleton and its preparation method and application
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A precursor compound, nitrogen heterocyclic carbene technology, applied in the direction of hydrocarbons, hydrocarbons, organic compounds/hydrides/coordination complex catalysts, etc. In the initial stage and other problems, to achieve the effect of superior reactivity
Active Publication Date: 2021-01-12
ZHEJIANG UNIV CITY COLLEGE
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[0003] For now, whether it is monodentate or bidentate chiral NHC ligands developed by research groups at home and abroad, its basic structural units are mainly based on the structure of five-membered ring imidazole or dihydroimidazole, among which as one of the representative skeletons The research on benzimidazole carbene ligands is less and is still in its infancy
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Embodiment 1
[0071] Preparation and characterization of compound Ⅱ-1:
[0072]
[0073] Dissolve compound Ⅰ-1 (521 μL, 4 mmol) and triethylamine (1112 μL, 8 mmol) in dry dichloromethane (40 mL), stir at room temperature for 5 minutes, then add tert-butyldimethylsilyl chloride (663 mg, 4.4 mmol ), after continuing stirring for 5 minutes, 4-dimethylaminopyridine (489 μL, 4 mmol) was added and reacted at room temperature for 3 hours. The reaction solution was evaporated to dryness under reduced pressure, and the mixture was separated by column chromatography (CH 2 Cl 2 :CH 3 OH=80:1~50:1), 656 mg of yellow oily substance II-1 was obtained with a yield of 71%. 1 H NMR (500MHz, CDCl 3 )δ: 3.76(dd, J=9.8, 3.2Hz, 1H), 3.40–3.31(m, 1H), 2.57(dd, J=8.8, 3.2Hz, 1H), 0.91(d, J=3.0Hz, 18H ), 0.07(s,6H).
Embodiment 2
[0075] Preparation and characterization of compound Ⅱ-2:
[0076]
[0077] The preparation conditions were the same as in Example 1, yellow oil, and the yield was 85%; 1 H NMR (500MHz, CDCl 3 )δ: 7.38(dd, J=8.3, 1.3Hz, 2H), 7.36–7.32(m, 2H), 7.29–7.24(m, 1H), 4.08(dd, J=8.4, 3.9Hz, 1H), 3.73 (dd, J=9.8, 4.0Hz, 1H), 3.53 (dd, J=9.8, 8.4Hz, 1H), 0.94–0.86(m, 9H), 0.03(t, J=2.2Hz, 6H).
Embodiment 3
[0079] Preparation and characterization of compound Ⅱ-3:
[0080]
[0081] The preparation conditions were the same as in Example 1, yellow oil, and the yield was 88%; 1 H NMR (500MHz, CDCl 3 )δ:7.33–7.28(m,2H),7.25–7.19(m,3H),3.59(dd,J=9.7,4.4Hz,1H),3.45(dd,J=9.7,6.5Hz,1H),3.10 (m,1H),2.80(dd,J=13.4,5.3Hz,1H),2.52(dd,J=13.4,8.4Hz,1H),0.94–0.91(m,9H),0.09–0.05(m,6H ).
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Abstract
The invention discloses chirality n-heterocyclic carbine precursor compound with benzoglioxaline frameworks and a preparation method and application thereof. Five steps of reaction can simply and effectively compound a series of chirality benzoglioxaline carbine precursor compound with novel structures, oxygen-containing functional groups containing lone pair electrons are be introduced into substituent groups of chirality side chains, the ligands can serve as bi-dentate ligands to combine with a metal center to form a complex compound, excellent reactive activation can show up in a metalcatalysisreaction system, and a catalytic product with a high-mapping isomer can be hopefully obtained in an asymmetric reaction.
Description
technical field [0001] The invention relates to the field of organic synthesis, in particular to a chiral nitrogen-heterocyclic carbene precursor compound with a benzimidazole skeleton and a preparation method and application thereof. Background technique [0002] The research history of N-heterocyclic carbenes (NHCs) can be traced back to Wanzlick’s first report in 1962, but it was not until 1991 that Arduengo et al. first isolated and obtained stable NHC monomers—imidazole-2-carbene, NHCs Ligand research has attracted widespread attention. Compared with phosphine ligands, azacarbene ligands have the following characteristics: 1) Stronger σ-donating properties and weaker π-accepting properties enable NHC to form more stable metal complexes with transition metals, and exhibit Better air and thermodynamic stability; 2) Different from the spatial layout of the "edge-to-face" phosphine ligand, the five-membered nitrogen heterocyclic carbene ligand has a wedge-shaped near-plana...
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