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Poly-N-heterocyclic carbene transition metal complexes and N-heterocyclic carbene transition metal complexes for carbon-sulfur and carbon-oxygen coupling reactions

A transition metal, heterocyclic carbene technology, applied in the formation/introduction of nickel organic compounds, sulfhydryl/thioether group, formation/introduction of ether group/acetal group/ketal group, etc., can solve the problem of low activity and catalyst. Problems such as low loading and many synthesis steps

Inactive Publication Date: 2010-03-31
AGENCY FOR SCI TECH & RES
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Problems solved by technology

However, disadvantages of such catalysts supported on polymers or mesoporous materials have also been reported, including low activity, many synthesis steps, low catalyst loading, and other disadvantages.

Method used

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  • Poly-N-heterocyclic carbene transition metal complexes and N-heterocyclic carbene transition metal complexes for carbon-sulfur and carbon-oxygen coupling reactions
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  • Poly-N-heterocyclic carbene transition metal complexes and N-heterocyclic carbene transition metal complexes for carbon-sulfur and carbon-oxygen coupling reactions

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Embodiment

[0081] All solvents purchased from commercial suppliers were used as received unless otherwise stated. in Eppendorf TM Centrifugal separation was performed on a centrifuge 5810R (4000rpm, 10min). Using an Agilent equipped with a split sampling capillary injection system and a flame ionization detector TM The 6890N Series Gas Chromatograph performs gas-liquid chromatography. Using Shimadzu TM GCMS QP2010 for gas chromatography-mass spectrometry (GC-MS) analysis. Use ELAN TM 9000 / DRC system for inductively coupled plasma mass spectrometry (ICP-MS) analysis. The progress of the catalytic reaction can usually be monitored by GC or GC-MS analysis of a reaction sample.

[0082] Synthesis of Ni(0)-p-NHC Catalyst

[0083] In the glove box, 82.5 mg of Ni(COD) 2(COD = cyclooctadiene) (0.3 mmol) was added to a THF suspension of polyimidazocarbene (p-Im) A (1 g). The mixture was stirred at room temperature for 16 hours. The suspension was then filtered and washed with DMF (...

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Abstract

Methods for carbon-sulfur (C S) or carbon-oxygen (C-O) coupling reactions are provided. The methods involve the use of a transition metal complex comprising a heterocyclic carbene ligand complexed with a transition metal. Transition metal complexes comprising a heterocyclic carbene ligand complexed with nickel are also provided. The nickel heterocylic carbene complexes may be used for C-S or C-O coupling reactions.

Description

[0001] This application claims the benefit of US Provisional Patent Application No. 60 / 924,164, filed May 2, 2007, which is hereby incorporated by reference in its entirety. technical field [0002] The present invention relates to a poly N-heterocyclic carbene (p-NHC) transition metal complex and N-heterocyclic carbene (NHC) transition metal for carbon-sulfur (C-S) and carbon-oxygen (C-O) coupling reactions Complexes. The present invention also relates to p-NHC nickel complexes and NHC nickel complexes that can be used in C-S and C-O coupling reactions. Background technique [0003] Organosulfur chemistry has received increasing attention due to the auxiliary role of sulfur-containing groups in organic synthesis methods. The aryl-sulfur bond is also a common functional group in many pharmaceutically active compounds. However, until a series of palladium organophosphine (Pd-PR 3 ) catalysts (including those developed by Buchwald, Hartwig, and others (see, for example, M.M...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/04C07B45/06C07F15/04
CPCC07B45/06C07F15/04C07B41/04Y02P20/582
Inventor 张玉根雅姬Y·邢赵兰
Owner AGENCY FOR SCI TECH & RES
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