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Synthetic method of a class of n-heterocyclic carbene borane adducts

A technology of heterocyclic carbene borane and synthesis method, which is applied in the field of synthesis of N-heterocyclic carbene borane adducts, can solve the problem that the yield is only 30-50%, and achieve high reaction efficiency and specific reaction good sex effect

Inactive Publication Date: 2020-06-02
LESHAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] This method needs to be carried out at a low temperature of -78°C, and dangerous BH is used in the reaction 3 Gas solution, the reaction time needs 12-24 hours, and the yield is only 30-50%

Method used

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  • Synthetic method of a class of n-heterocyclic carbene borane adducts
  • Synthetic method of a class of n-heterocyclic carbene borane adducts
  • Synthetic method of a class of n-heterocyclic carbene borane adducts

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Preparation of 1,3-Dimethylimidazolium Borane Adduct

[0027]

[0028] The reaction was carried out under the protection of Ar, and 0.006mol of 1,3-dimethylimidazole boron trifluoride adduct, 20mL of chloroform, 0.012mol of phenylsilane, 0.0003mol of tri(pentafluoro Phenyl) boron catalyst, after the addition of reactants is completed, stir the reaction at 40°C under Ar protection for 50min, NHC-BF 3 Complete conversion to NHC-BH 3 .

Embodiment 2

[0030] Preparation of 1-methyl-3-ethylimidazolium borane adduct

[0031]

[0032] The reaction was carried out under the protection of Ar, and 0.01mol of 1-methyl-3-ethylimidazole boron trifluoride adduct, 30mL of toluene, 0.02mol of butylsilane, 0.0005mol of tris (Pentafluorophenyl) boron catalyst, after the addition of reactants, stir the reaction at 40°C under Ar protection for 40min, NHC-BF 3 Complete conversion to NHC-BH 3 .

Embodiment 3

[0034] Preparation of 1-methyl-3-butylimidazolium borane adduct

[0035]

[0036] The reaction was carried out under the protection of Ar, and 0.5mol of 1-methyl-3-butylimidazole boron trifluoride adduct, 300mL of dichloromethane, 1mol of butylsilane, 0.025mol of Tris(pentafluorophenyl) boron catalyst, after the addition of the reactants, the reaction was stirred under Ar protection at 35°C for 60min, NHC-BF 3 Complete conversion to NHC-BH 3 .

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Abstract

The invention discloses a method for synthesizing an N-heterocyclic carbene borane adduct. The method comprises the following steps: adding x mol of a reaction substrate NHC-BF3, 2x-4xL of a reactionsolvent, x-6x mol of a reducing agent hydrosilane and 0.05-0.1x mol of a catalyst tri(pentafluorpheny)boron (BCF) into a reaction bottle under inert gas shielding, continuously stirring and reacting at a temperature of 25-50 DEG C for 30-60 minutes under inert gas shielding after reactant addition is completed, and completely converting the NHC-BF3 into NHC-BH3, wherein x ranges from 0.001 to 1. The method disclosed by the invention can be performed under mild conditions, the materials can be completely reacted within 30-60 minutes, and the reaction efficiency is high. The reaction specificityis excellent, any side reaction is avoided, and the reaction yield is close to 100%.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of a class of N-heterocyclic carbene borane adducts. Background technique [0002] N-Heterocyclic Carbene (NHC) is a new type of strong σ electron donor developed at the end of last century. As a kind of ligand, N-heterocyclic carbene has stable properties compared with traditional amine, ether and phosphorus ligands, and is not sensitive to air and water; the structure is diversified and easy to modify; the electron donating ability is strong, and the coordination bond is not easy Fracture; low toxicity, simple preparation, low cost and other advantages. It is precisely because of these characteristics of N-heterocyclic carbene that it has been widely used in homogeneous catalysis, new materials, and antibacterial drugs. [0003] Azacyclic carbene borane adduct (NHC-BH 3 ) is a class of highly active carbene adducts that have been reported more i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/02
Inventor 陈俏田冲杨金明聂万丽马克西姆李杰温志国
Owner LESHAN NORMAL UNIV