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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

On-surface azide-alkyne cycloaddition on Au(111).

Oscar Díaz Arado1, Harry Mönig, Hendrik Wagner

  • 1Physikalisches Institut, Westfälische Wilhelms-Universität Münster , Wilhelm-Klemm-Strasse 10, 48149 Münster, Germany.

ACS Nano
|September 20, 2013
PubMed
Summary

On-surface cycloaddition reactions between azides and alkynes were achieved on a gold surface. This method regioselectively forms 1,4-triazoles, enabling new organic nanomaterials.

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Synthesis of Substrate-Bound Au Nanowires Via an Active Surface Growth Mechanism
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Published on: July 18, 2018

Area of Science:

  • Organic Chemistry
  • Surface Science
  • Materials Science

Background:

  • The azide-alkyne cycloaddition is a key reaction in organic synthesis.
  • Controlling reactions on surfaces is crucial for fabricating nanomaterials.

Purpose of the Study:

  • To investigate the [3+2] cycloaddition of azides and alkynes on a Au(111) surface.
  • To understand the role of the gold surface in the reaction mechanism.
  • To explore the potential for creating functional organic nanomaterials.

Main Methods:

  • On-surface reactions performed under ultrahigh vacuum conditions.
  • High-resolution scanning tunneling microscopy (STM) for imaging reaction products.
  • Density functional theory (DFT) simulations to model reaction pathways and energetics.

Main Results:

  • Successful [3+2] cycloaddition reactions between azides and alkynes were observed at room temperature.
  • The reactions exhibited high regioselectivity, forming 1,4-triazoles.
  • DFT simulations indicated the Au(111) surface acts as a 2D template, not a catalyst.

Conclusions:

  • The Au(111) surface facilitates regioselective on-surface azide-alkyne cycloaddition at room temperature.
  • The gold surface acts as a physical constraint, guiding the reaction without direct catalytic involvement.
  • This approach holds significant promise for the surface-assisted synthesis of organic nanomaterials.