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Dialkylborane amine complexes

A technology of alkylborane amines and complexes, which is applied in the field of new dialkylborane amine complexes, which can solve problems such as difficult large-scale processing, steric volume hindering coordination, and not being separated.

Inactive Publication Date: 2009-09-16
BASF AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another undesirable property of dialkylboranes is the pyrophoric nature of the isolated solids, making it difficult to handle these compounds on a large scale
The EDA adducts of diisopentylborane and diisopinepinocampylborane were prepared in ether and THF, respectively, but were not isolated
However, the steric bulk of diethylaniline prevents its coordination with 9-BBN or even diethylborane

Method used

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  • Dialkylborane amine complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: Preparation of 9-BBN-5-ethyl-2-picoline complex in THF:

[0067] 1.21 g (0.01 mol) of 5-ethyl-2-methylpyridine was added to 20 ml of a 0.5M 9-BBN (0.01 mol) solution in THF at 0-5°C within 15 minutes. of the reaction mixture 11 B NMR spectrum no longer shows the signal of 9-BBN at 27.8ppm, but a new doublet (80Hz) signal appears at d=-1.3, attributed to 9-BBN-5-ethyl-2-picoline Complexes. Part of the THF was removed under vacuum to leave a concentrate, about 60 wt% 9-BBN-5-ethyl-2-picoline complex. 11 B NMR spectrum shows the product as a broad singlet at d = -0.8 (98% purity).

Embodiment 2

[0068] Example 2: Preparation of 9-BBN-5-ethyl-2-picoline complex in hexane:

[0069] 49.7 g (0.41 mol) of 5-ethyl-2-methylpyridine was added to 820 ml of a 0.5M 9-BBN (0.41 mol) solution in hexane at 0-5°C over 3.5 hours. of the reaction mixture 11 B NMR spectrum shows a new broad singlet signal at d=-0.5, assigned to 9-BBN-5-ethyl-2-picoline complex (IR spectrum in hexane: BH stretching vibration 2300- 2400cm -1 ). The solvent was distilled off under vacuum from half of the prepared hexane solution to leave an amber pyrophoric liquid, 47.5 g (95% yield). 11 The BNMR spectrum shows a broad singlet at d = -1.6 (95% purity) assigned to the product.

Embodiment 3

[0070] Example 3: Preparation of bis(2,5-dimethylhex-4-en-3-yl)borane-2-picoline complex in THF:

[0071] 2,5-Dimethyl-2,4-hexadiene (4.64g, 40mmol) was added to borane-tetrahydrofuran complex (20ml, 1M, 20mmol BH 3 )middle. After hydroboration was complete, 2-picoline (1.83 g, 20 mmol) was added to the solution of bis(2,5-dimethylhex-4-en-3-yl)borane. The bis(2,5-dimethylhex-4-en-3-yl)borane-2-picoline complex is shown at d = -3.2 11 B NMR signal (broad singlet, 85% purity).

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Abstract

The present invention relates to new dialkylborane amine complexes, a process for the synthesis of new dialkylborane amine complexes, solutions comprising new dialkylbo- rane amine complexes and a method of using new dialkylborane amine complexes for organic reactions.

Description

field of invention [0001] The present invention relates to new dialkylborane amine complexes, a method for synthesizing new dialkylborane amine complexes, solutions comprising new dialkylborane amine complexes and new dialkylborane amine complexes Methods for the use of amine complexes in organic reactions. Background of the invention [0002] Dialkylborane (R 2 BH) are valuable reagents for regioselective hydroboration reactions because boron atoms are only added to the less hindered carbon atoms of the carbon-carbon double bond. In addition, dialkylboranes with chiral alkyl substituents, such as diisopinocampheylborane (Ipc) 2 BH), which can be effectively used for the asymmetric reduction of ketones. [0003] However, the poor solubility of dialkylboranes in non-polar and polar solvents sometimes hinders their application. In nonpolar solvents, dialkylborane compounds generally exist as hydrogen-bridged dimers. Unfortunately, even the use of coordinating solvents suc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07B31/00
CPCC07F5/027C07F5/02C07B31/00
Inventor E·伯克哈特
Owner BASF AG
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