Video Experimental Relacionado
Updated: Feb 6, 2026
11:09
Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
11.2K
Hidrotiolación catalítica: acoplamiento regioselectivo y enantioselectivo de tiolos y dienos
Xiao-Hui Yang1, Ryan T Davison1, Vy M Dong1
1Department of Chemistry , University of California-Irvine , Irvine , California 92697 , United States.
Journal of the American Chemical Society
|August 10, 2018
Resumen
Una nueva reacción catalizada por rodio permite la adición selectiva de tiolos a 1,3-dienos, formando valiosos sulfuros alílicos. Este método eficiente funciona con materias primas de petróleo y diversos grupos funcionales.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Química del petróleo
Sus antecedentes:
- Los 1,3-dienos son componentes versátiles en la síntesis orgánica.
- Las reacciones de hidrotiolación son importantes para crear compuestos que contienen azufre.
- Los métodos eficientes y selectivos para la funcionalización de dienes son muy buscados.
Objetivo del estudio:
- Desarrollar una nueva hidrotiolación catalizada por el rodio de 1,3-dienes.
- Para lograr la adición selectiva de tiolos al doble enlace más sustituido.
- Demostrar la utilidad del método con materias primas derivadas del petróleo.
Principales métodos:
- Reacción de hidrotiolación catalizada por el rodio.
- Utilizó varios 1,3-dienes, incluidos los que se encuentran en las materias primas del petróleo.
- Tiolos utilizados para las reacciones de adición.
Principales resultados:
- Se han sintetizado con éxito sulfuros alilicos secundarios y terciarios.
- Alcanzó una alta selectividad para la adición al doble enlace más sustituido.
- Tolerancia demostrada del catalizador a una amplia gama de grupos funcionales.
- Se ha informado de una baja carga del catalizador de hasta 0,1 mol %.
Conclusiones:
- La hidrotiolación catalizada por rodio desarrollada es un método eficiente y selectivo para sintetizar sulfuros alílicos.
- La aplicabilidad de la reacción a las materias primas del petróleo y la tolerancia del grupo funcional la hacen valiosa para aplicaciones industriales.
- Este trabajo proporciona una nueva vía sintética para importantes compuestos organosulfurados.
Videos de Conceptos Relacionados
02:33Preparation and Reactions of Thiols
7.6K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
7.6K
01:29Diels–Alder Reaction: Characteristics of Dienes
5.4K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
5.4K
01:19Turnover Number and Catalytic Efficiency
21.6K
The turnover number of an enzyme is the maximum number of substrate molecules it can transform per unit time. Turnover numbers for most enzymes range from 1 to 1000 molecules per second. Catalase has the known highest turnover number, capable of converting up to 2.8×106 molecules of hydrogen peroxide into water and oxygen per second. Lysozyme has the lowest known turnover number of half a molecule per second.
Chymotrypsin is a pancreatic enzyme that breaks down proteins during digestion....
Chymotrypsin is a pancreatic enzyme that breaks down proteins during digestion....
21.6K
01:07Catalytically Perfect Enzymes
5.1K
The theory of catalytically perfect enzymes was first proposed by W.J. Albery and J. R. Knowles in 1976. These enzymes catalyze biochemical reactions at high-speed. Their catalytic efficiency values range from 108-109 M-1s-1. These enzymes are also called 'diffusion-controlled' as the only rate-limiting step in the catalysis is that of the substrate diffusion into the active site. Examples include triose phosphate isomerase, fumarase, and superoxide dismutase.
Most enzymes...
Most enzymes...
5.1K
01:16Structure of Conjugated Dienes
7.5K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
7.5K
01:28Stability of Conjugated Dienes
4.5K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
4.5K