2.7. Hydroxylation Reactions of Allenes 3282 2.8. Hydroamination Reactions of Allenes 3284 2.9. Hydrothiolation of Allenes 3284 2.10. Hydroalxoxylation of Alkenes and 1,3-Dienes 3286 2.11. Hydroamination of Alkenes and 1,3-Dienes 3287 2.12. Hydrothiolation of Conjugated Olefins 3289 3. Activation of Carbonyl/Imine Groups and Alcohols 3289 3.1. Condensation Reactions 3289 3.2. Addition Reactions 3291 3.3. Aldol Reactions 3294 3.4. Hydroand Carbosilylation Reactions 3295 3.5. Nucleophilic Substitution Reactions of Alcohols 3297 4. Gold-Catalyzed C-H Bond Functionalization 3297 4.1. Csp3-H Bond Functionalization 3298 4.2. Csp2-H Bond Functionalization 3299 4.3. Csp-H Bond Functionalization 3304 5. Gold-Catalyzed Selective Reductions 3305 5.1. Catalytic Hydrogenation of Alkenes 3306 5.2. Selective Reductions of R, -Unsaturated Carbonyl Groups and 1,3-Dienes 3306

Alternative synthetic methods through new developments in catalysis by gold.

Catalysis by Palladium Pincer Complexes

Catalysis by Supported Gold Nanoparticles: Beyond Aerobic Oxidative Processes

the National Natural Science Foundation of China (21073208);the Chinese Academy of Sciences

Nano-Gold Catalysis in Fine Chemical Synthesis

The first decade of the 21 century evidenced the explosive growth of homogeneous gold catalysis. The unique versatility and efficiency of gold metal complexes are clearly indicated by the numerous reports regarding their application in various organic transformations. Key to the success of homogeneous gold catalysis is the ability of gold(I) and gold(III) to act as soft carbophilic Lewis acids towards C C multiple bonds. This high carbophilicity translates to a relatively low oxophilic character and a kinetically labile carbon-metal bond, which allows efficient catalyst turnover. In addition, the high oxidation potential between gold(I) and gold(III) makes the gold catalysts inert from air oxidation. Therefore, compared with other transition metal catalysts, gold complexes could catalyze reactions under very mild conditions (tolerates air or moisture), giving excellent chemoselectivity, wide functional group compatibility and high efficiency. However, despite its high efficiency in alkyne and allene activation, gold catalysts, like many other transition metal complexes, inherit some limitations that prevent them from being “perfect.” Two clearly identified challenges in gold catalysis are a) rather poor thermal stability due to disproportionation of the metal cation and b) difficulty in asymmetric transformations. In the past several years, efforts have been made by various research groups to overcome these challenges. Significant progress has been made, which has given this very hot topic in catalytic research strong momentum for an even more promising future. Major breakthroughs in asymmetric gold catalysis are certainly expected in the coming decade and this Minireview, by highlighting recent advances, aims to facilitate progress in this fascinating field of research.

Recent Advances in Asymmetric Gold Catalysis

The ONN-tridentate unsymmetrical pincer 2- [6- (pyrrolidin-1 -ylmethyl)pyridin-2-yl]phenol and N-tert-butyl-1-{[6-(2-hydroxyphenyl)pyridin-2-yljmethyl)pyrrolidine-2-carboxamide ligands were synthesized by an easy method in high purity and good yields. All the organic compounds were characterized by elemental analysis, mass spectrometry, IR and 1 H and 13 CNMR spectroscopy. Palladium(II) and gold(III) complexes have been prepared as air-stable solids, with the ONN-tridentate ligand after deprotonation of the hydroxy group, the coordination of the metal ion is completely stereospecific and gives rise to only one diastereoisomer. These complexes were shown to be very active catalysts in the hydrogenation (80 % ee was achieved with the chiral gold complex), hydrosilylation and C-C coupling, Suzuki and Heck, reactions, under mild conditions.

New Pyridine ONN‐Pincer Gold and Palladium Complexes: Synthesis, Characterization and Catalysis in Hydrogenation, Hydrosilylation and CC Cross‐Coupling Reactions

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New Pyridine ONN‐Pincer Gold and Palladium Complexes: Synthesis, Characterization and Catalysis in Hydrogenation, Hydrosilylation and CC Cross‐Coupling Reactions