Pd-NHC (PEPPSI)
Complexes: Synthetic Utility and Computational Studies into Their
Reactivity

Michael G. Organ; Gregory A. Chass; De-Cai Fang; Alan C. Hopkinson; Cory Valente

doi:10.1055/s-2008-1067225

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Synthesis 2008(17): 2776-2797
DOI: 10.1055/s-2008-1067225

SPECIALTOPIC

Pd-NHC (PEPPSI) Complexes: Synthetic Utility and Computational Studies into Their Reactivity

Michael G. Organ*^a, Gregory A. Chass^b, De-Cai Fang^c, Alan C. Hopkinson^a, Cory Valente^a
^a Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada
e-Mail: organ@yorku.ca;
^b School of Chemistry, University of Wales, Bangor LL57 2UW, UK
^c College of Chemistry, Beijing Normal University, Beijing 100875, P. R. of China

Further Information

Publication History

Received 1 July 2008
Publication Date:
13 August 2008 (online)

Abstract
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Abstract

This review concentrates on the results obtained thus far in cross-coupling reactions utilising Pd-PEPPSI-IPr (pre)catalyst. Results from computational studies expose possible factors behind the high reactivity of this complex, as well as mechanistic details for the IPr-Pd-mediated alkyl-alkyl Negishi cross-coupling.

1 Introduction

2 Evolution to Pd-PEPPSI Complexes

2.1 Background of NHCs; Unraveling Electronic and Steric Components

2.2 Design and Preparation of Pd-PEPPSI Complexes

2.3 Mechanism of Activation and Role in the Catalytic Cycle

3 Cross-Coupling Results with Pd-PEPPSI Complexes

3.1 General Cross-Coupling Scheme

3.2 The Suzuki-Miyaura Reaction

3.3 The Kumada-Tamao-Corriu Reaction

3.4 The Negishi Reaction

3.5 Buchwald-Hartwig-Yagupol’skii Amination

4 Theory and Computation

4.1 Theory

4.2 Computation

4.3 Geometric Structure

4.4 Reaction Profile

4.5 Interactions

4.6 Atoms-in-Molecules

5 Conclusions

Key words

palladium - cross-coupling - PEPPSI - computation

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