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Method for efficiently catalyzing selective boronation reaction of five-membered heterocycle
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A five-membered heterocyclic and selective technology, which is applied in the field of highly efficient catalytic borylation of five-membered heterocyclic rings, can solve the problems of unfavorable practical application and large application limitations
Inactive Publication Date: 2020-04-21
TAIZHOU UNIV
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Although the above methods have achieved certain success, most of them involve excessive metal catalyst dosage and by-product formation, especially all the above boronation reactions involve the use of toxic organic solvents, which lead to large limitations in the application of this type of reaction and are not conducive to practical applications.
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Embodiment 1
[0009] Embodiment 1, wherein reaction substrate is as follows:
[0010] Reaction substrate structure formula:
[0011]
[0012] Under argonatmosphere, the metal complex (0.01mol%), the reaction substrate (1.0mol), and borane (1.0mol) were sequentially added to a 10mL sealed tube, and heated and stirred in an oil bath at 120°C for 24 hours. After the reaction was completed, the heterocyclic boronic acid ester product was separated by column chromatography under an air environment, and the yield was 79%. NMR data of the product: 1 H NMR (400MHz, CDCl 3 )δ7.63(d, J=4.0Hz, 1H), 7.57(d, J=4.0Hz, 1H), 7.40(s, 1H), 7.34(t, J=8.0Hz, 1H), 7.23(t, J=8.0Hz,1H),1.39(s,12H).
Embodiment 2
[0013] Embodiment 2, wherein reaction substrate is as follows:
[0014] Reaction substrate structure formula:
[0015]
[0016] Under argonatmosphere, the metal complex (0.01mol%), the reaction substrate (1.0mol), and borane (1.0mol) were sequentially added to a 10mL sealed tube, and heated and stirred in an oil bath at 120°C for 24 hours. After the reaction was completed, the heterocyclic boronic acid ester product was separated by column chromatography under an air environment, and the yield was 85%. NMR data of the product: 1 H NMR (400MHz, CDCl 3 )δ7.18(d,J=2.0Hz,1H),7.07(d,J=2.0Hz,1H),3.89(s,3H),1.34(s,12H).
Embodiment 3
[0017] Embodiment 3, wherein reaction substrate is as follows:
[0018] Reaction substrate structure formula:
[0019]
[0020] Under an argonatmosphere, the metal complex (0.05mol%), the reaction substrate (1.0mol), and borane (1.0mol) were sequentially added to a 10mL sealed tube, and heated and stirred in an oil bath at 120°C for 12 hours. After the reaction was completed, the heterocyclic boronic acid ester product was separated by column chromatography under an air environment, and the yield was 99%. NMR data of the product: 1 H NMR (400MHz, CDCl 3 )δ7.49(d,J=8.0Hz,1H),7.35(s,2H),7.06(d,J=8.0Hz,1H),2.47(s,3H),1.39(s,12H).
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Abstract
The invention relates to a method for efficiently catalyzing a selective boronation reaction of a five-membered heterocycle. A heterocyclic borate product can be smoothly prepared through convenientlycatalyzing a selective boronation reaction of furan and thiophene derivatives and a cheap and easily available organic boronreagent under a mild condition by a cheap rutheniummetal complex taken asa catalyst. Compared with a reported method, the method of the invention has the obvious advantages of specific reaction selectivity, low catalyst dosage, convenience in operation, no need of addinga reaction solvent and the like, and an efficient and high-selectivity reaction strategy is provided for laboratory preparation or industrial production of the heterocyclic borate product.
Description
technical field [0001] The invention relates to a method for efficiently catalyzing a selective borylation reaction of a five-membered heterocyclic ring. Background technique [0002] Organoborates are important chemical intermediates and are widely used in the synthesis of drugs, natural products and polymers. At present, the effective methods for synthesizing organic borates are mainly traditional methods and transition metal-catalyzed cross-coupling reactions between halogenated hydrocarbons and boranes. However, these methods have many defects, such as: too many operating steps, and the substrates used are in natural reserves. Very limited etc. limit further development. If the borylation reaction of the C-H bond can be directly realized, it is really of great application value, such as: performing a direct C-H bond borylation reaction on a heterocyclic molecule to further transform it into a more complex organic heterocyclic compound, which has a high Atom economy. H...
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