Practical aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by N-methylimidazole as a Lewis base catalyst (2023)

Cited by (37)

  • The Aldol Reaction: Group IV Enolates (Mukaiyama, Enol Ethers)

    2014, Comprehensive Organic Synthesis: Second Edition

    Aldol reactions are among the most important carbon–carbon bond-forming reactions. Compared with commonly utilized enolates derived from group I and II elements, enolates based on group IV elements, such as silicon and tin, are relatively stable and isolable. They serve as convenient carbonyl equivalent donors through nucleophilic additions to aldehydes and ketones in the presence of even a substoichiometric amount of a Lewis acid catalyst. Asymmetric variants of these reactions have been well explored, and silicon enolates have played a vital role in the development of many useful chiral Lewis acid catalysts. Lewis base catalysts can also activate silicon enolates bearing electron-deficient silyl group to promote aldol reactions. This chapter covers aldol reactions using group IV enolates. A large portion of this chapter is devoted to the use of silicon enolates, whereas the rest of the chapter will discuss the use of tin, germanium, lead enolates in aldol reactions.

  • A DMAP-catalyzed mild and efficient synthesis of 1,2-dihydroquinazolines via a one-pot three-component protocol

    2014, Tetrahedron Letters

    An efficient and simple method for the synthesis of 1,2-dihydroquinazolines catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP) from readily available aromatic or heteroaromatic aldehydes, 2-aminobenzophenone, and ammonium acetate under mild conditions is described. The scope and limitations of the method are discussed.

  • Aldol condensations of a variety of different aldehydes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system

    2013, Cuihua Xuebao/Chinese Journal of Catalysis

    Citation Excerpt :

    (Video) 2017/08/14 100 0015

    The practical applications of poly(N-vinylimidazole) (PVIm) are wide and varied, ranging from dyestuffs, catalysts, corrosion inhibitors, and ion exchange resins to their application in quenching media and metal ion complexation reactions [43]. N-Methylimidazole has been used as a Lewis base catalyst for the aldol condensation reactions of trimethylsilyl enolate with a range of different aldehydes [44,45]. In a continuation of our ongoing research towards the development of new catalysts and methods for organic synthesis [46–52], we recently used PVIm as an efficient solid Lewis base catalyst for the N-Boc protection of amines as well as the acetylation of alcohols, phenols, thiols, and amines under solvent-free conditions [53,54].

    An ultrasound-assisted aldol condensation reaction has been developed for a range of ketones with a variety of aromatic aldehydes using poly(N-vinylimidazole) as a solid base catalyst in a liquid-solid system. The catalyst can be recovered by simple filtration and reused at least 10 times without any significant reduction in its activity. The reaction is also amenable to the large scale, making the procedure potentially useful for industrial applications.

  • Base-catalyzed reactions of silyl enolates with carbonyl compounds are an attractive variant of conventional directed aldol reactions. Over the past two decades, the reaction has gained prominence due to its inherent advantage for stereoselective manipulations. The present review provides a brief account of developments in this area. Various approaches are grouped together in order to provide the salient features of each conceptual development. It appears that the methods which generate nascent chiral enolates or cationic siliconium species have the biggest influence on the stereoselectivity.

  • Solvent-free Mukaiyama-aldol condensation catalyzed by Ce-Al-MCM-41 mesoporous materials

    2011, Microporous and Mesoporous Materials

    Citation Excerpt :

    Again, the product selectivity was found almost ∼ 100% in each case. The reaction rate in Mukaiyama-aldol condensations has been found to depend upon the nature of the solvent employed for a reaction [5,14,18,36–40]. Therefore, the condensation of benzaldehyde with methyl trimethylsilyl dimethylketene acetal was studied using different solvents as reaction medium and employing sample F (Si/Ce = 59, Si/Al = 33) as a representative catalyst (Fig. 11).

    MCM-41 samples containing Ce4+ and Al3+ in the network, designated as Cex–Al–MCM-41 (x=0.0–0.04), were synthesized and characterized systematically. These samples exhibited higher catalytic activity for Mukaiyama-aldol condensations to produce β-hydroxy carbonyl compounds under the solvent free conditions, compared to the samples containing either of the two cations. The product yield was found to depend on the electron donating/withdrawing characteristics of reactant molecules being responsible for the observed trend. Series of solvents were also investigated but considerably high yield of aldol products (∼95%) could be achieved without using any solvents. In all the cases, the selectivity was found to be 100%, typical of such Mukaiyama-aldol condensations. The higher catalytic activity of Cex–Al–MCM-41 is explained on the basis of certain new acid sites generated due to co-incorporation of Ce and Al cations.

  • A recyclable fluoroalkylated 1,4-disubstituted [1,2,3]-triazole organocatalyst for aldol condensation of aldehydes and ketones

    2011, Journal of Fluorine Chemistry

    A new fluoroalkylated 1,4-disubstituted [1,2,3]-triazole was prepared and acted as an organocatalyst for aldol condensation of different ketones with various aldehydes. Aldol condensation proceeded efficiently in the presence of catalytic amount of fluoroalkylated [1,2,3]-triazole. The catalyst could be easily recovered by fluorous solid-phase extraction with excellent purity and reused for three runs with slightly decrease in its activity.

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Copyright © 2006 Elsevier Ltd. All rights reserved.


What is an aldol reaction with an aldehyde and a ketone? ›

Aldol condensation: An addition reaction between two aldehydes, two ketones, or an aldehyde and a ketone, resulting in a β-hydroxy aldehyde or a β-hydroxy ketone. Subsequent dehydration produces an α,β-unsaturated aldehyde or ketone. The addition step without subsequent dehydration is an aldol reaction.

What is the aldol reaction of an aldehyde? ›

'Aldol' is an abbreviation of aldehyde and alcohol. When the enolate of an aldehyde or a ketone reacts at the α-carbon with the carbonyl of another molecule under basic or acidic conditions to obtain β-hydroxy aldehyde or ketone, this reaction is called Aldol Reaction.

What is an example of an aldol reaction? ›

Uses and Applications of Aldol reaction

Structural aldol products are found in many essential molecules, whether naturally occurring or synthetic. For example, the aldol reaction has been used in the large-scale production of the commodity chemical pentaerythritol and the synthesis of the heart disease drug Lipitor.

What is the acid catalyzed aldol reaction mechanism? ›

Aldol Condensation Acid Catalyzed Mechanism

Under acidic conditions an enol is formed and the hydroxy group is protonated. Water is expelled by either and E1 or E2 reaction. When performing both reactions together always consider the aldol product first then convert to the enone.

What is the aldol condensation reaction of an aldehyde and an aldehyde? ›

Aldol condensation occurs in aldehydes having α-hydrogen with a dilute base to give β-hydroxy aldehydes called aldols. This reaction is most commonly known as aldol condensation. If the condensation reaction occurs between two different carbonyl compounds it is called crossed aldol condensation.

What is the product of aldol condensation of aldehyde and ketone? ›

An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to give a conjugated enone.

What are the four steps in the aldol reaction? ›

Step 1: The hydroxide ion deprotanates the aldehyde reversibly. Step 2: Enolate ion 1 adds to the unreacted aldehyde. Step 3: Alkoxide ion 2 is protonated by water. Step 4: Aldol 3 is an enolizable aldehyde.

What does the enolate formed during the aldol reaction act as? ›

The aldol reaction unites two carbonyl compounds to form a β-hydroxy-carbonyl product, where one carbonyl compound acts as a nucleophilic donor via its enolate or enol form and the other, a ketone or an aldehyde, acts as an electrophilic acceptor.

How many steps are in an aldol reaction? ›

Aldol reaction: its chemistry and mechanism. Typically, aldehydes and ketones undergo an aldol reaction. This reaction involves 3 basic steps: Step 1: Electrophilic attack of a base at the alpha-carbon (C α​start subscript, α, end subscript) of the aldehyde or ketone to generate an “enolate” carbanion.

What is aldol reaction in simple words? ›

Aldol (aldehyde + alcohol) reaction — Reaction of aldehyde (or ketone) enolate with another molecule of the aldehyde (or ketone) in the presence of NaOH or KOH to form β-hydroxy aldehyde (or ketone).

What are the 2 possible aldol products? ›

Propanal on aldol condensation gives 2-methylpent-2-enal. From cross aldol condensation of Ethanal and Propanal,it forms 2products, one when ethanol acts as enolate ion and one where propanal acts as enolate ion. The two cross aldol products are- 2-methylbut-2-enal and Pent-2-enal.

What is the formula for the aldol? ›

Aldol | C4H8O2 | CID 7897 - PubChem.

What is the first step in the aldol condensation reaction? ›

Step 1: Protonation of the oxygen of the carbonyl group occur. Step 2: The water molecule behaving as a base will remove the acidic α hydrogen leading to the formation of Enol. Step 3: The enol attacks a protonated carbonyl group of a second ketone molecule.

Can aldol reaction be catalyzed by acid? ›

Treating an aldehyde or ketone with Br2 in the presence of strong acid (HBr) will form a new C-Br bond on the alpha carbon. No reaction occurs in the absence of strong acid. Acid can catalyze the aldol condensation.

What is the mechanism of aldol condensation step by step? ›

A three step mechanism:
  1. Step 1: Enolate formation.
  2. Step 2: Nucleophilic attack by the enolate.
  3. Step 3: Protonation.
Jan 22, 2023

What types of aldehydes undergo aldol condensation? ›

The aldehydes that have alpha hydrogen atoms undergo aldol condensation reaction.

What is the difference between aldol reaction and aldol condensation? ›

The reaction of carbonyl compound enolates with aldehydes and ketones to form a β-hydroxy carbonyl compound is the Aldol Reaction, if conditions result in a subsequent dehydration to form the α,β-unsaturated compound, then the reaction is termed the Aldol Condensation (loss of a molecule of water).

What is the difference between aldol and aldol condensation? ›

The key difference between aldol addition and aldol condensation is that aldol addition refers to the addition of a ketone enolate or an aldehyde enolate to a carbonyl compound, whereas aldol condensation refers to the loss of a water molecule from an aldol product to form an α,β-unsaturated carbonyl compound.

What is the final product of the aldol condensation of two molecules of aldehyde? ›

The product formed for aldol condensation is called β-hydroxy aldehyde or β-hydroxy ketone.

What is the product formed by the reaction of an aldehyde with a primary amine? ›

The product of reaction with primary amine and aldehyde is imine.

Which aldehyde and ketones not give aldol condensation? ›

Formaldehyde HCHO does not contain alpha hydrogen atom. Hence, it does not undergo aldol condensation reaction.

What is the catalyst for aldol condensation? ›

(10) It is generally accepted that aldol condensation on TiO2 is catalyzed by Lewis acid–base site pairs (Ti–O pairs) and proceeds via enolation of the aldehyde or ketone to form an enolate intermediate, followed by C–C coupling between the enolate and an adjacent aldehyde or ketone.

What is the purpose of adding base in the aldol condensation reaction? ›

Aldol Condensation under Basic Conditions

To begin the condensation reaction, a base deprotonates the carbon next to the carbonyl group on the first molecule, forming an enolate molecule. This creates a nucleophilic carbon, due to the newly freed electron pair as a result of the deprotonation.

What is the rate determining step in the aldol condensation reaction? ›

The rate determining step of aldol condensation reaction is the first slower step i.e. the formation of carbanion.

Can an aldehyde form an enolate? ›

Enolates can be formed from aldehydes and ketones, but also from esters, amides, nitriles and many other carbonyl-containing compounds. When an additional electron-withdrawing group is present on the alpha-carbon, enolates become much easier to form.

What is the enolate formation in aldol condensation? ›

In aldol condensation, an enolate ion reacts with another carbonyl compound to form a conjugated enone. The process occurs in two parts: an aldol reaction, which forms an aldol product, and a dehydration reaction, which removes water to form the final product.

Does acetaldehyde give aldol condensation reaction? ›

So, yes Acetaldehyde undergoes Aldol condensation reaction.

What is the order of aldol reaction? ›

When methanol or other hydrophilic organic compound was not used as a co-solvent for the aldol condensation reaction, the reaction was first order in aldehyde concentration. However, methanol made the reaction second order in aldehyde concentration.

What is required for aldol reaction? ›

Therefore, a necessary requirement for the aldol reaction is that the aldehyde be enolizable (i.e. have a proton on the alpha carbon). No proton → no enolate → no aldol. hover to see some examples of enolizable vs non enolizable aldehydes or click on this link.

Which compound can be formed from an aldol reaction? ›

The fundamental transformation in the aldol reaction is a dimerization of an aldehyde (or ketone) to form a beta-hydroxy aldehyde (or ketone).

What is aldol also known as? ›

In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or "aldol" (aldehyde + alcohol), a structural unit found in many naturally occurring molecules and pharmaceuticals.

How many types of aldols can be formed by following reaction? ›

There are four possible products of aldol condensation between acetaldehyde and propanal. The aldol of acetaldehyde with itself will be one of the products. Similarly, one will be propanal with propanal. The final two aldols will be cross aldols.

What are the major product of cross aldol reaction? ›

The major cross aldol product of the following reaction is :CH3CHO+CH3CH2CHO.

What functional group is in an aldol? ›

Aldol: A molecule containing an aldehyde (or ketone) and alcohol functional groups separated by one carbon (i.e., a β-hydroxy aldehyde or β-hydroxy ketone).

What functional groups are in the aldol? ›

The enone product of an aldol condensation is versatile because it contains two functional groups (alkene & carbonyl) which can be subject to further reactions. Among many possible reactions, an enone can undergo hydrogenation to produce an aldehyde or ketone.

Why is the aldol reaction often called an aldol condensation? ›

If the reaction is warmed, it can then lose a molecule of water to form an alkene-aldehyde or alkene-ketone, known as an alpha,beta-unsaturated aldehyde or ketone. In this case the overall reaction is known as an aldol condensation.

What are the limitations of aldol condensation? ›

The aldol condensation is not limited to aldehydes. Ketones may also be used. In fact, it is possible to use two different carbonyl compounds to form a crossed aldol product. One limitation of the crossed aldol reaction is the fact that multiple products can form due to the presence of multiple different α-hydrogen.

What is acid catalyzed aldol condensation with aldehyde? ›

It is a condensation reaction in which dimerisation of aldehyde or ketone occurs. In it, an enolate ion reacts with a carbonyl compound to form a beta-hydroxy aldehyde or beta-hydroxy ketone, accompanied by elimination of water molecule to yield a conjugated enone.

What is the difference between acid catalyzed and base catalyzed aldol? ›

The mechanisms for acid catalyzed aldol condensation and base catalyzed aldol condensation is significantly different. While bases activate the nucleophile, acids activate the electrophile in the reaction. It must be noted that aldol condensation is an integral mechanism of Robinson annulation as well.

Can aldol condensation be of acid and base catalysed? ›

The actual reason why aldol condensation is catalysed by both acids and bases is because both the carbanion (formed in the presence of an acid) and enol (formed in the presence of a base) act as nucleophile and participates in aldol condensation.

What is the chemical reaction for aldehydes and ketones? ›

Aldehydes can be oxidized to carboxylic acids with chromium trioxide/Jones reagent. Ketones can undergo oxidative cleavage with very strong oxidizing agents such as potassium permanganate. Ketones can be oxidized to esters by peroxycarboxylic acids in a reaction known as Baeyer-Villiger oxidation.

Which reaction is given by both aldehyde and ketone? ›

Hence 2,4-DNP test is given both by aldehydes and ketones.

What is the typical reaction of ketones and aldehydes? ›

ALDEHYDES AND KETONES. With the exception of oxidation of aldehydes, the reactions of aldehydes and ketones is dominated by nucleophilic addition. Reduction of the non-polar C=C or C C bonds in alkenes and alkynes respectively, can be accomplished with (non-polar) hydrogen gas, H2.

What can both aldehyde and ketone react with? ›

Aldehydes and ketones both react with Tollen's reagent to form silver mirror.

What are the 4 chemical reactions of aldehydes and ketones? ›

Hint: Both the aldehyde and ketone group has carbonyl group, i.e., $>C=O$ group and they give many chemical reactions like Nucleophilic addition reaction, reduction reaction, oxidation reaction, halogenations, and reaction with alkalis.

What is the product formed by the reaction of an aldehyde? ›

The product of reaction with primary amine and aldehyde is imine. For example, acetaldehyde reacts with methyl amine to form (E)-N-ethylidenemethanamine. Was this answer helpful?

What is the reaction of aldehydes and hydrogen? ›

In reduction reactions of aldehydes and ketones we add hydrogen across the double bond. That is, a hydrogen atom will be added to each atom of the double bond, converting the aldehyde or ketone into an alcohol.

What is the difference between aldehyde and ketone with reaction? ›

Despite both having a carbon atom at the centre, the fundamental difference between an aldehyde and ketone lies in their distinct chemical structure. An aldehyde combines to an alkyl on one side and a Hydrogen atom on the other, while the ketones are known for their double alkyl bonds on both sides.

What is the conclusion of the reaction of the aldehydes and ketones? ›

Conclusion. The difference between aldehydes and ketones are the presence of a hydrogen atom attached to the carbon-oxygen double bond in the aldehyde. It is because ketone do not have that hydrogen. The presence of that hydrogen atom makes aldehydes very easy to oxidize and makes it as a strong reducing agent.

What are the two tests to distinguish aldehydes from ketones? ›

1. Tollen's Test: Aldehydes give positive Tollen's test (silver mirror) while ketones do not give any reaction. 2. Fehling's test: Aliphatic aldehydes on treatment with Fehling's solution give a reddish brown precipitate (positive result) while aromatic aldehydes and ketones do not.

How do you remember reactions of aldehydes and ketones? ›

The three important preparation methods for aldehydes and ketones can be remembered using 'A Clean New Bed'.

What is the nucleophilic substitution reaction of aldehyde and ketone? ›

The nucleophilic addition reaction between hydrogen cyanide (HCN) and carbonyl compounds (generally aldehydes and ketones) results in the formation of cyanohydrins. Base catalysts are often used to increase the rate of the reaction.

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