Use of n-butyllithium for catalyzing hydroboration of imine and borane

Patent metadata

Field	Value
Publication number	US-11845068-B2
Application number	US-202117225063-A
Country	US
Kind code	B2
Filing date	Apr 7, 2021
Priority date	Oct 8, 2018
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

The present invention relates to the use of n-butyllithium for catalyzing the hydroboration of an imine and a borane. A catalyst, the borane and the imine are sequentially stirred and mixed uniformly, and are reacted for 1-2 h; the mixture is exposed to air to terminate the reaction; and the reaction liquid is subjected to reduced pressure to remove the solvent, so as to obtain a borate with different substituents. The n-butyllithium disclosed in the present invention can be used for catalyzing the hydroboration of the imine and the borane in high activity under room temperature conditions, the amount of the catalyst is only 4-5 mol % of the molar weight of the imine, and the yield of the reaction can reach 90% or more.

First claim

The invention claimed is:

1. A method of preparing a borate ester comprising:
reacting an imine with a borane in an organic solvent and in the presence of n-butyllithium as a catalyst at room temperature under anhydrous, oxygen-free, and inert gas conditions for 1-2 hours; and
stirring in air to stop reaction and to obtain the borate ester.

2. The method of claim 1 , wherein:
the imine has the following structure:

the borane is pinacol borane;
the borate ester has the following structure:

and
R 1 and R 2 are independently selected from the group consisting of halogen, methyl and methoxy.

3. The method of claim 1 , wherein the organic solvent is tetrahydrofuran.

4. The method of claim 1 , wherein an amount of n-butyllithium is 4% to 5% of a molar amount of the imine.

5. The method of claim 1 , wherein a molar ratio of the imine to the borane is 1:1 to 1:1.2.

6. The method of claim 5 , wherein the molar ratio of the imine to the borane is 1:1.2.

Assignees

• Univ Soochow

Inventors

• Xue Mingqiang
• Yan Dandan

Classifications

• B01J31/12 Primary

  containing organo-metallic compounds or metal hydrides · CPC title

• C07F5/04

  Esters of boric acids · CPC title

• C07F5/022 Primary

  without C-boron linkages · CPC title

• B01J31/122

  Metal aryl or alkyl compounds · CPC title

• B01J2231/323

  Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation · CPC title