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Related Concept Videos

Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.3K
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.
3.3K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.9K
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.
9.9K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.2K
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...
4.2K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.7K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
19.7K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.7K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
2.7K
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

11.4K
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...
11.4K

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Related Experiment Video

Updated: Nov 16, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination.

P Veeraraghavan Ramachandran1, Shivani Choudhary1, Aman Singh1

  • 1Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States.

The Journal of Organic Chemistry
|February 19, 2021
PubMed
Summary

A new solvent-free reductive amination method uses trimethyl borate and ammonia borane to efficiently convert aldehydes and ketones with amines into valuable products.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Area of Science:

  • Organic Chemistry
  • Green Chemistry

Background:

  • Reductive amination is a crucial reaction in organic synthesis.
  • Traditional methods often require harsh conditions or toxic reagents.
  • Developing sustainable and efficient amination protocols is essential.

Purpose of the Study:

  • To develop a novel, solvent-free reductive amination protocol.
  • To utilize readily available and safer reagents.
  • To achieve high yields for a broad substrate scope.

Main Methods:

  • The reaction employs sub-stoichiometric amounts of trimethyl borate as a promoter.
  • Ammonia borane serves as the reductant in a solvent-free system.
  • Aldehydes and ketones react with aliphatic and aromatic amines.

Main Results:

  • High-to-excellent yields were obtained for the reductive amination products.
  • The method is effective for both aliphatic and aromatic amines.
  • The solvent-free conditions contribute to a greener synthetic approach.

Conclusions:

  • Solvent-free reductive amination is efficiently achieved using trimethyl borate and ammonia borane.
  • This method offers a sustainable and high-yielding alternative for amine synthesis.
  • The protocol is versatile, applicable to various aldehydes, ketones, and amines.