Video Experimental Relacionado

Updated: Sep 9, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Acceso fácil a los alquenos trifluorometílicos multi-sustituidos mediante la deshidroxifluoración de los alcoholes

Zhi-Qiang Li¹, Zaixin Wang¹, Cheng-Qiang Wang¹

¹Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, State Key Laboratory of Material-Oriented Chemical Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China. cqwang08@njtech.edu.cn.

Organic & biomolecular chemistry

|August 29, 2025

Resumen

La síntesis de fluoruros alilicos es crucial, pero el control de la regioselectividad es difícil. Este estudio introduce un nuevo método para la deshidroxifluoración específica de los alcoholes difluoroalilo utilizando el reactivo de Olah.

Área de la Ciencia:

Química orgánica
Química de la fluoración

Sus antecedentes:

La deshidroxifluoración de los alcoholes alilicos es una vía clave para los fluoruros alilicos.
El control de la regioselectividad en esta reacción es un desafío persistente en la química sintética.

Objetivo del estudio:

Desarrollar un método para la deshidroxifluoración específica de los alcoholes 3,3-difluoroalilo.
Abordar el desafío de la regioselectividad en la síntesis de fluoruro alílico.

Principales métodos:

Se utilizó el reactivo de Olah para la reacción de deshidroxifluoración.
Se emplearon condiciones de reacción suaves para lograr la transformación.

Principales resultados:

Se demostró una deshidroxifluoración regiospecífica inducida por el efecto del flúor.
Se han sintetizado con éxito productos específicos de fluoruro alilico con alta regioselectividad.

Conclusiones:

El método desarrollado ofrece una vía directa y eficaz a los fluoruros alilicos regiodefinidos.
Los efectos del flúor se pueden aprovechar para controlar la regioselectividad en las reacciones de deshidroxifluoración.

Más Videos Relacionados

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Videos de Conceptos Relacionados

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Base-Promoted α-Halogenation of Aldehydes and Ketones

Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base. The reaction begins with the abstraction of α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Conversion of Alcohols to Alkyl Halides

Conversion of Alcohols to Alkyl Halides

This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...

Preparation of Alcohols via Substitution Reactions

Preparation of Alcohols via Substitution Reactions

Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...