Work

Protodepalladation as a Strategic Elementary Step in Catalysis

Year: 2018

Type: article

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

Source: Synthesis

DOI: 10.1055/s-0037-1611064

Authors: Keary Engle, Miriam O’Duill

Institutions: Scripps Research Institute, Ollscoil na Gaillimhe – University of Galway

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Combinatorial, Catalytic Functionalization of Alkenes and Alkynes