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A Theoretical Study of Pd-Catalyzed C-C Cross-Coupling ReactionsAn Asymmetric Suzuki-Miyaura Reaction Mechanism

A Theoretical Study of Pd-Catalyzed C-C Cross-Coupling Reactions: An Asymmetric Suzuki-Miyaura... [The Suzuki-Miyaura reaction, commonly known simply as Suzuki coupling, is one of the most practiced types of C–C cross-coupling reactions. In 2008, the group of Profs. Fern\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}ndez and Lassaletta reported that the use of the (S,S)-2,5-diphenyl-pyrrolidine-derived glyoxal bis-hydrazone ligand in catalysts of the type [PdCl\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$_2$$\end{document}(L)] in conjunction with Cs\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$_2$$\end{document}CO\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$_3$$\end{document} as base and toluene as solvent, allows the asymmetric Suzuki-Miyaura coupling of a broad variety of substrates in high yields and enantioselectivities. Motivated by these striking results, we decided to investigate theoretically the reported Suzuki-Miyaura coupling that led to the highest yield and enantioselectivity. The major objective of this theoretical study is to give an explanation of the origin of the enantioselectivities experimentally observed. With this aim, the full catalytic cycle for the above mentioned coupling was computed. All the results of obtained in this work are presented in this chapter. This work has been carried out in collaboration with the experimental group of Profs. Rosario Fern\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}ndez and J. M. Lassaletta from the Universidad de Sevilla and the CSIC de Sevilla, respectively.] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png

A Theoretical Study of Pd-Catalyzed C-C Cross-Coupling ReactionsAn Asymmetric Suzuki-Miyaura Reaction Mechanism

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Publisher
Springer International Publishing
Copyright
© Springer International Publishing Switzerland 2013
ISBN
978-3-319-01489-0
Pages
113 –133
DOI
10.1007/978-3-319-01490-6_6
Publisher site
See Chapter on Publisher Site

Abstract

[The Suzuki-Miyaura reaction, commonly known simply as Suzuki coupling, is one of the most practiced types of C–C cross-coupling reactions. In 2008, the group of Profs. Fern\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}ndez and Lassaletta reported that the use of the (S,S)-2,5-diphenyl-pyrrolidine-derived glyoxal bis-hydrazone ligand in catalysts of the type [PdCl\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$_2$$\end{document}(L)] in conjunction with Cs\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$_2$$\end{document}CO\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$_3$$\end{document} as base and toluene as solvent, allows the asymmetric Suzuki-Miyaura coupling of a broad variety of substrates in high yields and enantioselectivities. Motivated by these striking results, we decided to investigate theoretically the reported Suzuki-Miyaura coupling that led to the highest yield and enantioselectivity. The major objective of this theoretical study is to give an explanation of the origin of the enantioselectivities experimentally observed. With this aim, the full catalytic cycle for the above mentioned coupling was computed. All the results of obtained in this work are presented in this chapter. This work has been carried out in collaboration with the experimental group of Profs. Rosario Fern\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}ndez and J. M. Lassaletta from the Universidad de Sevilla and the CSIC de Sevilla, respectively.]

Published: Oct 5, 2013

Keywords: Oxidative Addition; Reductive Elimination; Organoboron Compound; Oxidative Addition Reaction; Calculated Gibbs Energy

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