Related Experiment Video
Updated: Dec 14, 2025

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Synthesis and Reactivity of Stable Alkyl-Pd(IV) Complexes Relevant to Monodentate N-Directed C(sp3)-H
William G Whitehurst1, Matthew J Gaunt1
1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
Abstract:
Alkyl-Pd(IV) complexes are frequently invoked in the proposed mechanisms of Pd-catalyzed C(sp3)-H functionalization reactions, though few examples of Pd(IV) complexes containing cyclopalladated substrates have been isolated due to the instability of the high-valent Pd(IV) center. Herein, we report the synthesis of stable and isolable OCO pincer-supported alkyl-Pd(IV) complexes containing cyclopalladated alkylamine and oxime frameworks, which represent the first examples of alkyl-Pd(IV) complexes derived from the oxidation of cyclopalladated monodentate N-donor substrates. The aminoalkyl-Pd(IV) complexes reacted efficiently with O- and N-nucleophiles to afford γ-functionalized alkylamine products. A mechanistic study of the nucleophile-mediated reductive elimination was conducted using an oxime-derived Pd(IV) complex, which revealed the intermediacy of a previously unexplored anionic Pd(IV) species.
More Related Videos
06:26Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
Published on: August 17, 2018
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Radical Reactivity: Steric Effects
Along with electronic...
Preparation and Reactions of Sulfides
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cycloaddition Reactions: Overview
Radical Substitution: Allylic Bromination