Related Experiment Video
Updated: Jun 9, 2025
09:14
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
12.0K
Multifunctionalization of Alkenyl Alcohols via a Sequential Relay Process.
Chong Liu1, Ling Wang2, Haibo Ge1
1Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409, United States.
Journal of the American Chemical Society
|October 29, 2024
Summary
Researchers developed a new method for synthesizing valuable aryl-substituted aliphatic amines. This sequential relay process efficiently creates diverse arylalkylamines through arylamination, deuterated arylamination, and methylenated arylamination.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- Aryl-substituted aliphatic amines are crucial building blocks in various chemical applications.
- Developing efficient synthetic routes for these compounds remains a significant challenge in organic chemistry.
Purpose of the Study:
- To establish a novel and practical method for the synthesis of diverse arylalkylamines.
- To explore new functionalization strategies for carbonyl groups in synthetic transformations.
Main Methods:
- Sequential relay process involving multifunctionalization of alkenyl alcohols.
- Development of a novel functionalization mode for carbonyl groups enabling deuterium and methylene incorporation.
Main Results:
- Successful synthesis of multifarious arylalkylamines via arylamination, deuterated arylamination, and methylenated arylamination.
- Demonstrated wide functional group tolerance and applicability to various alkenol and amine structures.
Conclusions:
- The developed methodology offers a versatile and efficient approach to arylalkylamine synthesis.
- This work provides new tools for the transformation of carbonyl groups and the construction of complex amine structures.
Related Concept Videos
02:15Preparation of Alcohols via Addition Reactions
6.1K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.1K
01:38Preparation of Alcohols via Substitution Reactions
5.7K
Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
5.7K
02:48Conversion of Alcohols to Alkyl Halides
7.1K
This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
7.1K
03:08Hydroboration-Oxidation of Alkenes
7.9K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
7.9K
02:35Acid-Catalyzed Dehydration of Alcohols to Alkenes
19.3K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
19.3K
01:22Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
1.9K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.9K