Merging Organocatalysis and Gold Catalysis—A Critical Evaluation of the Underlying Concepts

Abstract

While both organocatalysis and gold catalysis have their roots deeply entrenched in the landscape of modern organic chemistry, an exciting trend in the complementary merging of organocatalysis and especially Au(I) catalysis has emerged in the last four years. This niche area has been developing rapidly and this minireview serves to pin-point the fundamental concepts guiding reaction design in these binary catalytic systems. Moreover, the proven synthetic utility of organo/Au(I) multicatalytic systems in accessing molecular frameworks, previously a challenge to single catalytic systems, has resulted in this new concept permeating numerous areas of organocatalysis, such as primary/secondary amine, Brønsted acid, hydrogen-bonding as well as N-heterocyclic carbene (NHC) catalysis. The first detailed account of these recent developments is systematically presented.

Ligand Exchange at a Gold(I) Carbene Complex

“…Then the suspension was filtered through Celite, and the solid residue was washed with acetonitrile. Removal of the solvent in vacuo gave [5] [48] and refinement [49] were achieved with standard Patterson and Fourier techniques. All non-hydrogen atoms were refined with anisotropic displacement parameters.…”

“…N-heterocyclic carbenes (NHCs) have been in the focus of interest [1 -4] due to their application as organocatalysts [5,6] or as ligands in transition metal complexes [1 -4, 7, 8], many of which are active in various homogeneous catalytic reactions [9,10]. NHC complexes feature an impressive stability against air, heat and moisture.…”

Aminoindolines versus Quinolines: Mechanistic Insights into the Reaction between 2-Aminobenzaldehydes and Terminal Alkynes in the Presence of Metals and Secondary Amines

“…21 We believe that the present study could also help in understanding other cooperative catalytic processes involving other metal catalysts (especially Au and Pt) and secondary amines. 22 ■ ASSOCIATED CONTENT…”

Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers

“…Over the past few years, the combination of dual catalytic systems into asymmetric one-pot tandem procedures has been paid much attention due to the fact that this could provide effective access to valuable chiral complex structures from simple precursors via sequential processes. Compared with the costly organo/metal dual catalytic system-induced one-pot sequential processes [6][7][8][9][10][11][12][13], organo/organo catalysis is more experimentally simple and environmentally friendly which could support the development of green and sustainable chemistry [14][15][16][17][18][19][20].…”