Get 20M+ Full-Text Papers For Less Than $1.50/day. Start a 14-Day Trial for You or Your Team.

Learn More →

A Theoretical Study of Pd-Catalyzed C-C Cross-Coupling ReactionsThe Cu-Free Sonogashira Reaction Mechanism

A Theoretical Study of Pd-Catalyzed C-C Cross-Coupling Reactions: The Cu-Free Sonogashira... [The palladium-catalyzed Sonogashira reaction is one of the most important and widely used methods for preparing arylacetylenes and conjugated enynes, [1–6] which are precursors for natural products, pharmaceuticals, and materials with specialized optical and electronic properties [7–12]. The purpose of the work reported in this chapter was to weigh up the reaction mechanisms proposed in the literature and possible alternative pathways using a general model of the typical Pd-catalyzed copper-free Sonogashira reaction. To this aim, the Gibbs energy profiles of the different mechanistic proposals were computed by means of DFT calculations. Additionally, the effect of the electronic nature of the alkyne’s substituents over all the reaction pathways was also analyzed. This was examined for a set of substituents combining theoretical calculations and experiments. This work was carried out in collaboration with the experimental group of Prof. Carmen N\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$\acute{\mathrm{a}}$$\end{document}jera at the Universidad de Alicante.] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png

A Theoretical Study of Pd-Catalyzed C-C Cross-Coupling ReactionsThe Cu-Free Sonogashira Reaction Mechanism

Download PDF
22 pages

Loading next page...
 
/lp/springer-journals/a-theoretical-study-of-pd-catalyzed-c-c-cross-coupling-reactions-the-65cBI7xe3P
Publisher
Springer International Publishing
Copyright
© Springer International Publishing Switzerland 2013
ISBN
978-3-319-01489-0
Pages
89 –111
DOI
10.1007/978-3-319-01490-6_5
Publisher site
See Chapter on Publisher Site

Abstract

[The palladium-catalyzed Sonogashira reaction is one of the most important and widely used methods for preparing arylacetylenes and conjugated enynes, [1–6] which are precursors for natural products, pharmaceuticals, and materials with specialized optical and electronic properties [7–12]. The purpose of the work reported in this chapter was to weigh up the reaction mechanisms proposed in the literature and possible alternative pathways using a general model of the typical Pd-catalyzed copper-free Sonogashira reaction. To this aim, the Gibbs energy profiles of the different mechanistic proposals were computed by means of DFT calculations. Additionally, the effect of the electronic nature of the alkyne’s substituents over all the reaction pathways was also analyzed. This was examined for a set of substituents combining theoretical calculations and experiments. This work was carried out in collaboration with the experimental group of Prof. Carmen N\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$\acute{\mathrm{a}}$$\end{document}jera at the Universidad de Alicante.]

Published: Oct 5, 2013

Keywords: Energy Barrier; Ionic Mechanism; Phosphine Ligand; Anionic Mechanism; Reductive Elimination

There are no references for this article.