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A bonding model for gold(I) carbene complexes.

Diego Benitez¹, Nathan D Shapiro, Ekaterina Tkatchouk

¹Materials and Process Simulation Center, California Institute of Technology, Pasadena, California 91125 USA.

Nature Chemistry

|February 18, 2010

Summary

This summary is machine-generated.

Electrophilic gold complexes form intermediates with carbon-gold bonds. The bonding varies, influencing reactivity in reactions like gold-catalyzed cyclopropanation.

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Area of Science:

Organometallic chemistry
Catalysis
Reaction mechanisms

Background:

Electrophilic gold catalysis has grown significantly in the last decade.
Mechanisms often propose gold-stabilized cationic intermediates.
The precise nature of bonding in these intermediates is not fully understood.

Purpose of the Study:

To investigate the bonding characteristics of gold-stabilized intermediates.
To understand how bonding influences reactivity in gold catalysis.
To define the bonding continuum from gold-stabilized carbenes to carbocations.

Main Methods:

Computational analysis of bonding in gold-stabilized intermediates.
Varying carbene substituents and ancillary ligands to probe bonding.
Experimental validation using gold-catalyzed cyclopropanation reactions.

Main Results:

The carbon-gold bond exhibits a mix of sigma and pi-bonding character.
The overall bond order is generally less than or equal to unity.
Bonding characteristics are tunable by substituents and ligands, defining a carbene-carbocation continuum.

Conclusions:

The bonding in gold-stabilized intermediates is a spectrum, not a single state.
Substituent and ligand choice dictates the position on this bonding continuum.
This bonding-reactivity correlation is evident in gold-catalyzed cyclopropanation yields.