Protodepalladation as a Strategic Elementary Step in Catalysis

Miriam L. O’Duill; Keary M. Engle

doi:10.1055/s-0037-1611064

Synthesis, Table of Contents

Synthesis 2018; 50(24): 4699-4714
DOI: 10.1055/s-0037-1611064

review

Protodepalladation as a Strategic Elementary Step in Catalysis

Miriam L. O’Duill

^aSchool of Chemistry, NUI Galway, University Road, Galway H91 TK33, Ireland

^bDepartment of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States Email: keary@scripps.edu

,

Keary M. Engle *

^bDepartment of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States Email: keary@scripps.edu

› Author Affiliations

Abstract

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Abstract

Protodepalladation is the redox-neutral conversion of a C–Pd(II) bond into a C–H bond via reaction with a Brønsted acid. It is the microscopic reverse of Pd(II)-mediated C–H cleavage. In the context of catalytic reaction development, protodepalladation offers a means of converting organopalladium(II) intermediates into organic products without a change in oxidation state at the metal center. Hence, when integrated into catalytic cycles, it can be a uniquely enabling elementary step. The goal of this review is to provide an overview of protodepalladation, including exploration of different reaction types, discussion of literature examples, and analysis of mechanistic features. Our hope is that this review will stimulate other researchers in the field to pursue new applications of this underexploited step in catalysis.

1 Introduction

2 Mechanistic Considerations

3 Examples of Synthetically Enabling Protodepalladation Reactions

3.1 Alkenylpalladium Species

3.2 Arylpalladium Species

3.3 Palladium Enolates

3.4 Alkylpalladium Species

4 Conclusion

Key words

palladium - palladacycles - alkenes - alkynes - cyclization - transition metals - protonation - metalation

Full Text

References

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