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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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8.8K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.2K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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γ-Selective C(sp3)-H amination via controlled migratory hydroamination.

Changseok Lee1,2, Huiyeong Seo1,2, Jinwon Jeon1,2

  • 1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Korea.

Nature Communications
|September 28, 2021
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Summary

This study introduces a new method for remote alkene functionalization, enabling the addition of amine groups at the gamma-position of aliphatic chains through nickel-hydride-catalyzed chain walking.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Remote C(sp3)-H functionalization of alkenes is challenging, especially at the gamma-position.
  • Existing methods are limited to C-H bonds near polar groups.

Purpose of the Study:

  • To develop a novel method for gamma-selective C(sp3)-H amination of unactivated alkenes.
  • To enable late-stage functionalization of aliphatic chains.

Main Methods:

  • Nickel-hydride (NiH) catalyzed migratory formal hydroamination.
  • Chelation-assisted control using directing groups (e.g., 8-aminoquinoline).
  • Ligand and directing group optimization for olefin isomerization and amination selectivity.

Main Results:

  • Achieved gamma-selective amination of alkenes via controlled chain walking.
  • Demonstrated installation of various amine groups at the gamma-C(sp3)-H bond.
  • Extended the methodology to delta-selective amination using picolinamide substrates.
  • Investigated the mechanism and selectivity through experimental and computational studies.

Conclusions:

  • The developed NiH-catalyzed method provides a versatile route for remote C(sp3)-H amination.
  • This approach allows for late-stage synthesis of value-added gamma-aminated products.
  • The methodology offers precise control over functionalization site through directed chain walking.