Related Experiment Video
Updated: Oct 18, 2025
09:37
Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
9.8K
Imine Reduction with Me2S-BH3
Mohammad M Kamal1, Zhizhou Liu1,2, Siyuan Zhai1
1School of Chemistry, Faculty of Sciences, Monash University, Clayton 3800, Australia.
Molecules (Basel, Switzerland)
|September 28, 2021
Summary
Tetra-coordinate borohydride species are the active hydride donors in hydroboration reactions. Dimethyl sulfide-borane (Me₂S-BH₃) effectively reduces various imines, demonstrating its utility as a chemoselective hydroboration reagent.
Area of Science:
- Organic Chemistry
- Catalysis
- Boron Chemistry
Background:
- Hydroboration reactions utilize various catalysts for organic substrates like aldehydes, ketones, and imines.
- Emerging evidence indicates that tetra-coordinate borohydride species, generated from boron reagents, are the actual hydride donors.
Purpose of the Study:
- To investigate the potential of dimethyl sulfide-borane (Me₂S-BH₃) as a hydride donor for imine reduction.
- To evaluate the effectiveness and chemoselectivity of Me₂S-BH₃ in hydroboration of imines.
Main Methods:
- Reaction of various imines with dimethyl sulfide-borane (Me₂S-BH₃).
- Analysis of reaction products to determine chemoselectivity and efficiency.
Main Results:
- Dimethyl sulfide-borane (Me₂S-BH₃) was confirmed as an effective reagent for the hydroboration of a diverse range of imines.
- The reagent demonstrated significant chemoselectivity in these reduction reactions.
Conclusions:
- Tetra-coordinate borohydride species are the key intermediates in hydroboration.
- Dimethyl sulfide-borane (Me₂S-BH₃) serves as a potent and chemoselective reagent for imine hydroboration.
Related Concept Videos
01:20Amides to Amines: LiAlH4 Reduction
5.3K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
5.3K
00:55Nitriles to Amines: LiAlH4 Reduction
3.9K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.9K
01:38Preparation of Amines: Reductive Amination of Aldehydes and Ketones
3.2K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
3.2K
02:23Alcohols from Carbonyl Compounds: Reduction
11.2K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
11.2K
01:18Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
2.4K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.4K
02:26Preparation and Reactions of Sulfides
5.2K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.2K