Video Experimental Relacionado

Updated: Sep 9, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Foto/Sulfinamidación catalizada por el cobre de arenos y alquenos

Dan Liu¹, Jianlu Hu¹, Weida Li¹

¹School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.

Organic letters

|August 28, 2025

Resumen

Este estudio introduce un nuevo método fotocatalizado por cobre para la síntesis de sulfinamidas de arilo utilizando sales de sulfonio. Este enfoque eficiente permite una funcionalización suave y regioselectiva para el descubrimiento de fármacos y la síntesis de compuestos bioactivos.

Área de la Ciencia:

Química orgánica
Metodología sintética
Catálisis

Sus antecedentes:

Las sulfinamidas de arilo son bloques de construcción cruciales en productos farmacéuticos y agroquímicos.
Las rutas sintéticas existentes a menudo están limitadas por condiciones duras y reactivos prefuncionalizados.

Objetivo del estudio:

Desarrollar un método suave y eficiente para la sulfamidación de arilo.
Para permitir la funcionalización en etapa tardía de moléculas complejas.

Principales métodos:

La sulfinamidación fotocatalizada por el cobre de arenos y alquenos.
Se utilizan sales de arilo y alquenilo sulfonio como precursores de radicales.

Principales resultados:

Se han logrado condiciones de reacción leve con una amplia tolerancia de grupo funcional.
Se ha demostrado una funcionalización de fase tardía altamente regioselectiva.
Se ha facilitado el acceso a diversos derivados de arilo S ((IV) y S ((VI).

Conclusiones:

El método desarrollado ofrece una plataforma poderosa para el descubrimiento de fármacos.
Permite la síntesis modular de compuestos bioactivos con una mayor eficiencia.

Más Videos Relacionados

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Videos de Conceptos Relacionados

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

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,...

Amines to Sulfonamides: The Hinsberg Test

Amines to Sulfonamides: The Hinsberg Test

The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...

Amines to Alkenes: Hofmann Elimination

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...

Preparation of 1° Amines: Azide Synthesis

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...