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Related Concept Videos

C–C Bond Formation: Aldol Condensation Overview01:10

C–C Bond Formation: Aldol Condensation Overview

14.0K
Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
14.0K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.8K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

3.1K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
3.1K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

3.4K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
3.4K
C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

6.2K
The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
6.2K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.4K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
2.4K

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Related Experiment Video

Updated: Sep 19, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Automated Iterative N─C and C─C Bond Formation.

Theodore Tyrikos-Ergas1, Sevasti Agiakloglou1, Antonio J LaPorte1

  • 1Department of Chemistry, University of Illinois, Urbana, IL, 61820, USA.

Angewandte Chemie (International Ed. in English)
|June 18, 2025
PubMed
Summary
This summary is machine-generated.

Automated small molecule synthesis is advanced by a new CbzT group, enabling iterative N-C and C-C bond formation for modular assembly of complex compounds like Imatinib.

Keywords:
AutomationBlock chemistryBoronatesCbzTIDANitrogen iteration handle

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Area of Science:

  • Organic Chemistry
  • Chemical Engineering
  • Medicinal Chemistry

Background:

  • Small molecule discovery is crucial for societal challenges but hindered by manual synthesis.
  • Current automated methods like block chemistry excel at C-C bond formation but not nitrogen incorporation.
  • A need exists for versatile automated synthesis platforms that can handle diverse chemical structures.

Purpose of the Study:

  • To develop a novel chemical strategy for automated, modular small molecule synthesis.
  • To introduce a new iteration-enabling group for incorporating nitrogen atoms into automated synthesis.
  • To demonstrate the utility of this new method in synthesizing a clinically relevant drug.

Main Methods:

  • Development and application of the CbzT (p-TIDA boronate-substituted carboxybenzyl) group.
  • Iterative synthesis utilizing both C-C and N-C bond formations.
  • Automated modular assembly of building blocks.
  • Catch-and-release purification enabled by the CbzT group.

Main Results:

  • The CbzT group was successfully synthesized and characterized.
  • Automated modular synthesis of Imatinib (Gleevec) was achieved using iterative N-C and C-C bonds.
  • The CbzT group enabled reversible attenuation of nitrogen reactivity and facilitated purification.
  • The methodology expands the scope of automated small molecule synthesis.

Conclusions:

  • The CbzT group significantly advances automated modular synthesis by enabling nitrogen incorporation.
  • This approach facilitates the generalized and automated preparation of diverse small molecules.
  • The work supports the development of machine-amenable chemical synthesis strategies.