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Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

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,...

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...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

Regioselective Formation of Enolates

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.

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Regioselective Difunctionalization and Annulation of Ynamide.

Shubham Dutta¹, Rajendra K Mallick², Akhila K Sahoo¹

¹School of Chemistry, University of Hyderabad, Gachibowli, Hyderabad, Telangana, 500046, India.

Angewandte Chemie (International Ed. in English)

|April 8, 2023

Summary

Ynamides are powerful building blocks in organic synthesis, enabling the creation of complex molecules through difunctionalization and annulation reactions. This review highlights their versatility and mechanistic advancements for novel synthetic strategies.

Keywords:

Chelation Keteniminium Radical Regioselective 1,2-Difunctionalization Ynamide

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Heterocyclic Chemistry

Background:

Ynamides are versatile reagents in organic synthesis.
They facilitate access to complex molecular structures.
Key transformations include 1,2-difunctionalization and annulation.

Purpose of the Study:

To provide a systematic overview of ynamide difunctionalization and annulation reactions.
To discuss recent mechanistic breakthroughs and synthetic applications.
To highlight the potential of ynamides in synthesizing complex molecular architectures.

Main Methods:

Review of regioselective difunctionalization reactions.
Analysis of annulation reactions involving ynamides.
Discussion of multi-component and radical-triggered reactions.

Main Results:

Ynamides enable the formation of functionalized N-bearing olefins and heterocycles.
Regioselective difunctionalization and annulation reactions have been systematically reviewed.
Mechanistic insights into ynamide transformations have been elucidated.

Conclusions:

Ynamides are highly versatile building blocks for organic synthesis.
Advancements in ynamide chemistry expand substrate scope and synthetic possibilities.
Future prospects include the synthesis of intricate molecular architectures.