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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Cycloaddition Reactions: Overview

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.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Related Experiment Video

Updated: Jan 18, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Organosilicon Precursors for Efficient Aromatic Copper-Mediated Radiocyanation.

Jay S Wright¹, Richard Ma¹, Casey J McCarthy¹

¹Department of Radiology, University of Michigan, Ann Arbor, MI, 48109, USA.

Chem

|September 11, 2025

Summary

This study introduces a novel copper-mediated ¹¹C-cyanation reaction using aryl silanes for positron emission tomography (PET) radiomedicine production. This method enhances stability, safety, and efficiency in radiolabelling compared to existing techniques.

Keywords:

Carbon-11 Copper-Mediated Radiolabelling Nuclear Medicine Organosilane Positron Emission Tomography Radiochemistry Radiocyanation

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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

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

Published on: May 26, 2019

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Last Updated: Jan 18, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

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

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

Published on: May 26, 2019

Area of Science:

Radiochemistry
Nuclear Medicine
Organic Synthesis

Background:

Copper-mediated radiolabelling is crucial for developing positron emission tomography (PET) imaging agents.
Current methods face challenges in stability, reactivity, and toxicity, impacting radiomedicine production.

Purpose of the Study:

To develop a novel copper-mediated ¹¹C-cyanation reaction for (hetero)aromatic imaging agents.
To overcome limitations of existing radiolabelling techniques, improving safety and reproducibility.

Main Methods:

Utilized heptamethyltrisiloxanes as (hetero)aryl nucleophiles in a copper-mediated ¹¹C-cyanation reaction.
Demonstrated rapid ipso-radiocyanation with high conversions and improved stability/safety advantages.

Main Results:

Achieved superior conversions compared to related precursors for radiolabelling.
Successfully labelled multiple bioactive scaffolds relevant to preclinical and clinical PET imaging.
Reported an automated radiosynthesis of a κ-opioid receptor antagonist for clinical PET studies.

Conclusions:

Aryl silane precursors offer significant advantages for radiochemical space expansion.
This novel protocol enhances the production of PET nuclear medicines, improving safety and efficiency.