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Aluminium chloride-catalyzed dehydroboration of terminal alkynes

A technology of alkynes and aluminum chloride, which is applied in the field of dehydroboration of alkynes catalyzed by aluminum chloride, can solve the problems of expensive and complex synthesis methods, and achieve wide substrate universality and simple reaction process Easy to operate and highly active

Active Publication Date: 2022-03-01
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this type of reaction, metal catalysts such as Ir and Ag are relatively expensive. In addition to the reported AgCl salt catalysis, the synthesis methods of other metal catalysts are also relatively complicated. It is necessary to prepare corresponding auxiliary ligands or add additional organic bases as co-catalysts. Therefore, The catalytic pathway remains to be developed
[0003] As a common metal, aluminum has the advantages of cheap and easy to obtain, low toxicity, etc. So far, there has been no report on the use of cheap and easily available aluminum chloride to catalyze the dehydroboration reaction of terminal alkynes

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Aluminum chloride catalyzes the dehydroboration reaction of p-methylphenylacetylene and pinacol borane, and the process is as follows:

[0015] Under anhydrous and oxygen-free conditions, add 0.001mmol aluminum chloride, 1mmol p-toluene acetylene and 1.2mmol pinacol borane in sequence to a single-port reaction tube, add a stirrer and stir at 25°C for 1h, and obtain the product by nuclear magnetic spectrum The rate is 99%. 1 H NMR (CDCl 3 ,400MHz)δ=1.31(s,12H,BOCMe 2 ),2.33(s,3H,ArCH 3 ),7.10-7.12(m,2H,Ar-H),7.40-7.42(m,2H,Ar-H)ppm. 13 C NMR (CDCl 3 ,100.6MHz) δ=21.6,24.7,84.4,102.2,118.8,129.1,132.5,139.7ppm. 11 B NMR (CDCl 3 ,128.4MHz) δ=24.2ppm.

Embodiment 2

[0017] Aluminum chloride catalyzes the dehydroboration reaction of phenylacetylene and pinacol borane, and the process is as follows:

[0018] Under anhydrous and oxygen-free conditions, add 0.001mmol aluminum chloride, 1mmol phenylacetylene and 1.2mmol pinacol borane in sequence to a single-port reaction tube, add a stirrer and stir at 25°C for 10h, and the yield is 99% according to the nuclear magnetic spectrum . 1 H NMR (CDCl 3 ,400MHz)δ=1.31(s,12H,BOCMe 2 ),7.28-7.37(m,3H,Ar-H),7.51-7.53(m,2H,Ar-H)ppm. 13 C NMR (CDCl 3 ,100.6MHz) δ=24.7,84.4,101.8,121.9,128.3,129.4,132.5ppm. 11 BNMR (CDCl 3 ,128.4MHz) δ=24.2ppm.

Embodiment 3

[0020] Aluminum chloride catalyzes the dehydroboration reaction of p-fluorophenylacetylene and pinacol borane, and the process is as follows:

[0021] Under anhydrous and oxygen-free conditions, add 0.001mmol aluminum chloride, 1mmol p-fluorophenylacetylene and 1.2mmol pinacol borane in sequence to a single-port reaction tube, add a stirrer and stir at 25°C for 1h, and obtain the yield by nuclear magnetic spectrum 99%. 1 H NMR (CDCl 3 ,400MHz)δ=1.32(s,12H,BOCMe 2 ),6.99-7.03(m,2H,Ar-H),7.50-7.53(m,2H,Ar-H)ppm. 13 C NMR (CDCl 3 ,100.6MHz) δ=24.7,84.5,100.7,115.7,118.0,134.6,163.1ppm. 11 BNMR (CDCl 3 ,128.4MHz) δ=24.1ppm.

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PUM

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Abstract

The invention discloses an aluminum chloride-catalyzed dehydroboration method of terminal alkynes, and belongs to the technical field of dehydroboration of terminal alkynes. In the method, under anhydrous and oxygen-free conditions and no reaction solvent, terminal alkyne is added to aluminum chloride, and then pinacol borane is added to carry out dehydroboration reaction. The aluminum chloride catalyzes the reaction between the terminal alkyne and the pinacol borane with high activity, wide substrate universality, high reaction yield, and the catalyst is cheap and easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of dehydroboration of terminal alkynes, and in particular relates to a method for dehydroboration of terminal alkynes catalyzed by aluminum chloride. Background technique [0002] The hydroboration reaction of alkynes is one of the most commonly used methods for preparing olefinic boron compounds. The catalysts commonly used in the current technology are various metal catalysts, but the synthesis of metal catalysts is usually more complicated and the cost is higher. The dehydroboration reaction of terminal alkynes is an important method for the synthesis of terminal alkyne borides (Lee C, DeMott J C, Pell C J, etal. Chem. Sci., 2015, 6(11), 6572-6582. Lee C ,Zhou J,Ozerov O V.J.Am.Chem.Soc.,2013,135(9),3560-3566.Hu J,Liu L,Hu X,et al.Tetrahedron,2014,70(35),5815-5819) . There are many cases of catalyzing this type of reaction before, such as Ir, Ag, Cu and other metal catalysts. In this type of reaction, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C07F7/18
CPCC07F5/02C07F7/1804C07F7/1892
Inventor 马猛涛罗曼肖钤
Owner NANJING FORESTRY UNIV
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