Alkylborane derivative and synthesis method thereof

A technology for alkyl borane and derivatives, applied in the field of alkyl borane derivatives and synthesis thereof, can solve the problems of complicated procedures, many reaction steps, low reaction efficiency and the like, and achieves high reaction efficiency, simple operation and easy raw materials. the effect

Pending Publication Date: 2021-12-31
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses flammable and easily hydrolyzed trimethylboroxine, diborane, and toxic gas carbon monoxide, which has certain safety problems, and there are many reaction steps, complicated procedures, and relatively low reaction efficiency.

Method used

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  • Alkylborane derivative and synthesis method thereof
  • Alkylborane derivative and synthesis method thereof
  • Alkylborane derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] The synthetic method of alkyl borane derivatives, the steps are as follows:

[0076] In a 25 mL schlenk tube, add aliphatic carboxylic acid derivative compound 2a (0.2 mmol), bis-linked pinacolyl diborane (0.6 mmol), Pd(OPiv) in sequence under air 2 (0.02mmol), silver carbonate (0.6mmol), sodium bicarbonate (0.4mmol), 2-chloroquinoline (0.04mmol) and 2.0mL acetonitrile, stirred at 130°C for 24 hours. Separation by silica gel column chromatography (eluent is petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) to obtain polysubstituted alkyl borane derivatives, denoted as 1a (32.0mg, Yield 66%). The target product was confirmed by nuclear magnetic resonance and high-resolution mass spectrometry; the synthetic route is as follows:

[0077]

[0078] Compound Characterization Data

[0079] Alkylborane (1a), yellow liquid.

[0080] 1 H NMR (400MHz, CDCl 3 ) 1 H NMR (400MHz, CDCl 3 )δ9.87(s,1H),8.80(dd,J=14.9and5.2Hz,2H),8.13(d,J=8.1Hz,1H),7.60–7.37(m,3H),2.58(s,2H ...

Embodiment 2

[0082] The synthetic method of alkyl borane derivatives, the steps are as follows:

[0083] In a 25mL schlenk tube, add aliphatic carboxylic acid derivative compound 2b (0.2mmol), double pinacol diborane (0.6mmol), Pd(OPiv) in sequence under air 2 (0.02mmol), silver carbonate (0.6mmol), sodium bicarbonate (0.4mmol), 2-chloroquinoline (0.04mmol) and 2.0mL acetonitrile, stirred at 130°C for 24 hours. Separation by silica gel column chromatography (eluent is petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) to obtain polysubstituted alkylborane derivatives, denoted as 1b (48.0mg, Yield 62%). The target product was confirmed by nuclear magnetic resonance and high-resolution mass spectrometry; the synthetic route is as follows:

[0084]

[0085] Compound Characterization Data

[0086] Alkylborane (1b), yellow solid.

[0087] 1 H NMR (400MHz, CDCl 3 )δ 1 H NMR (400MHz, CDCl 3 )δ9.18(s,1H),8.98(m,1H),8.77(m,1H),8.18(m,1H),7.89(m,4H),7.68(s,1H),7.55(m,1H ),7.43(m,1H),4.48...

Embodiment 3

[0089] The synthetic method of alkyl borane derivatives, the steps are as follows:

[0090] In a 25 mL schlenk tube, add aliphatic carboxylic acid derivative compound 2c (0.2 mmol), double pinacol diborane (0.6 mmol), Pd(OPiv) in sequence under air 2 (0.02mmol), silver carbonate (0.6mmol), sodium bicarbonate (0.4mmol), 2-chloroquinoline (0.04mmol) and 2.0mL acetonitrile, stirred at 130°C for 24 hours. Separation by silica gel column chromatography (eluent is petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) to obtain polysubstituted alkyl borane derivatives, denoted as 1c (62.0mg, Yield 75%). The target product was confirmed by nuclear magnetic resonance and high-resolution mass spectrometry; the synthetic route is as follows:

[0091]

[0092] Compound Characterization Data

[0093] Alkylborane (1c), yellow solid. 1 H NMR (400MHz, CDCl 3 )δ 1 H NMR (400MHz, CDCl 3 )δ8.77–8.69(m,2H),8.45(m,1H),8.19(m,1H),7.62–7.53(m,2H),7.46(t,J=7.8Hz,1H),2.19(t ,J=6.0Hz,1H),1.87(m...

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Abstract

The invention provides an alkyl borane derivative and a synthesis method thereof. The method comprises the steps that an aliphatic carboxylic acid derivative and bis-pinacol diborane serve as initial reaction raw materials, palladium salt serves as a catalyst, silver salt serves as an oxidizing agent, C-H bond activation and one-step synthesis reaction are conducted in a solvent in the presence of alkali and an additive, the reaction has good regioselectivity, functional group diversity and wide applicability, amide groups in the skeleton structure of the alkyl borane derivative can be hydrolyzed to obtain corresponding carboxylic acid, alkyl boron groups can be further functionalized, and the alkyl borane derivative can be used as intermediates of structures of drugs and chemical products.

Description

technical field [0001] The invention relates to an alkyl borane derivative and a synthesis method thereof, belonging to the field of chemical organic synthesis. Background technique [0002] Boranes, especially alkylboranes, have become important intermediates in organic synthesis. Widely used in the formation of carbon-hydrogen bonds, carbon-oxygen bonds, carbon-halogen bonds, carbon-nitrogen bonds, carbon-carbon bonds and other chemical bonds. What is more prominent is that these reactions have excellent stereoselectivity, which is especially suitable for the stereosynthesis of many natural products such as steroids, terpenoids and hormones. Alkyl borane is the precursor of many functional molecules, and occupies an important position in the fields of organic synthesis, drug synthesis and natural product synthesis (Chem. Rev. 2010, 110, 890; Acc. Chem. Res. 2012, 45, 864). Organoborides can also be used as enzyme inhibitors (Drug Discovery Today 2003, 8, 307) and in boro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07D215/40
CPCC07F5/025C07D215/40
Inventor 娄江韩文佳李霞丁其军姜亦飞
Owner QILU UNIV OF TECH
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