Applications of Metal Nanopore Catalysts in Organic Synthesis

This account is dedicated to the memory of Professor Manfred Schlosser for his outstanding contributions to organometallic chemistry.

Abstract

Reducing the size of bulk metals to nanometer scale can result in the display of extraordinary physical and chemical properties. Typically, metal nanoparticles (MNPs) are prepared from metal atoms or metal salts and show remarkable catalytic properties. Metal nanopores (MNPores) are prepared through a totally reverse approach (from bulk metal to nanosized metal): alloy M¹M² is fabricated from metal M¹ and metal M², and then dealloying of M² results in a nanoporous framework of metal M¹. This account summarizes MNPore-catalyzed reactions developed in our group, and their comparison with other representative catalytic reactions.

1 Introduction

1.1 Fabrication and Structural Characteristics of Nanoporous Gold

2 Oxidation Reactions

2.1 Oxidation of Alcohols

2.2 Synthesis of Formamides Through Oxidative Coupling of Methanol with Amines

2.3 Oxidation of Silanes

3 Reduction Reactions

3.1 Semihydrogenation of Alkynes

3.2 Reduction of Quinoline

3.3 Reduction of Imines and Reductive Amination of Carbonyls

3.4 Reduction of α,β-Unsaturated Aldehydes

3.5 1,4-Hydrosilylation of Cyclic Enones

4 Formation of C–Si, C–B, and C–C Bonds Using Alkynes

4.1 Hydrosilylation of Alkynes

4.2 Diboration of Alkynes

4.3 Benzannulation Reaction

5 CuNPore-Catalyzed Click Reaction

6 Suzuki, Negishi and Heck Coupling Reactions

7 Concluding Remarks

Key words

metal nanoparticle catalysts - metal nanopore catalysts - nanoparticles - nanopores - heterogeneous - homogeneous - oxidation - reduction

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