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Catalysis

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

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(CAAC)Pd(py) Catalysts Disproportionate to Pd(CAAC)₂.

Nicola Marigo^1,2, Bernd Morgenstern¹, Andrea Biffis²

¹Coordination Chemistry, Saarland University, Campus C4.1, Saarbrücken D-66123, Germany.

Organometallics

|July 14, 2023

Summary

This summary is machine-generated.

New palladium catalysts using cyclic (alkyl)(amino)carbene ligands show high activity in Buchwald-Hartwig amination and diazene formation. These cyclic (alkyl)(amino)carbene complexes are effective catalysts for challenging cross-coupling reactions.

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Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Palladium complexes with N-heterocyclic carbene (NHC) ligands are established cross-coupling precatalysts.
Pyridine serves as a common ancillary ligand in these systems.

Purpose of the Study:

To investigate palladium complexes featuring cyclic (alkyl)(amino)carbene (CAAC) ligands as alternatives to NHC ligands.
To evaluate the catalytic performance of these CAAC-palladium complexes in cross-coupling reactions and diazene formation.

Main Methods:

Synthesis and characterization of palladium complexes bearing CAAC and pyridine ligands.
Evaluation of catalytic activity in Buchwald-Hartwig amination using aryl chlorides.
Assessment of catalytic performance in diazene formation from anilines in the presence of dioxygen.

Main Results:

The reduced form, (CAAC)Pd(py), disproportionates into (CAAC)2Pd0 and palladium nanoparticles.
CAAC-palladium complexes exhibit potent catalytic activity in Buchwald-Hartwig amination of aryl chlorides at 60 °C.
These complexes effectively catalyze diazene formation from anilines under aerobic conditions.
Catalytic activity in cross-coupling is comparable to NHC-supported complexes, but CAAC complexes excel in diazene synthesis.

Conclusions:

Cyclic (alkyl)(amino)carbene ligands can effectively replace N-heterocyclic carbene ligands in palladium precatalysts.
CAAC-palladium complexes are highly efficient catalysts for both Buchwald-Hartwig amination and aerobic diazene formation.
These findings expand the scope of ligands for palladium-catalyzed cross-coupling and related transformations.