Hydrosilylation of carbonyl and carboxyl groups catalysed by Mn(i) complexes bearing triazole ligands

Oriol Martínez-Ferraté,Basujit Chatterjee,Walter Leitner,Christophe Werlé

doi:10.1039/c9cy01738k

Abstract

Manganese(i) complexes bearing readily accessible triazole ligands are effective catalysts for the hydrosilylation of carbonyl and carboxyl compounds.

Highlights

In the last three decades, industrial breakthroughs in homogeneous catalysis mainly involved catalysts based on second- and third-row transition metals, which are rare elements, whose mining generates waste, and is often associated with low abundance and high costs
The excellent performance of the platinum group metals has overshadowed the potential of first-row transition metals, albeit they have been widely used in academia and industry at the early days of homogeneous catalysis
Triazole 2 was treated with bromopentacarbonylmanganeseIJI) in toluene at room temperature to provide the desired complex 3 in 46% yield

Summary

Introduction

The modern chemical industry mostly relies on catalysis for the synthesis of bulk materials and fine chemicals.1 In the last three decades, industrial breakthroughs in homogeneous catalysis mainly involved catalysts based on second- and third-row transition metals, which are rare elements, whose mining generates waste, and is often associated with low abundance and high costs.2 The excellent performance of the platinum group metals has overshadowed the potential of first-row transition metals, albeit they have been widely used in academia and industry at the early days of homogeneous catalysis. Of PhSiH3 and 2 mol% of complex 8 in THF at 80 °C for 3 hours led to moderate conversions (53%), with preferential formation of ethyl benzyl ether 11 (94%) relative to benzyl alcohol 10 (6%, entry 1). For catalyst 3, the selectivity towards the alcohol product 10 increased with decreasing temperature, albeit at the expense of conversion (entry 4, 8–10).

Results

Conclusion