Pd-Catalyzed Oxidative Functionalization of Alkenes, Arenes, and 1,3-Dienes Using Molecular Oxygen as the Terminal Oxidant

Abstract

This Account presents palladium-complex-catalyzed oxidative couplings mainly developed by the author’s group, including oxidative amination and silylation of terminal alkenes, direct oxidative arylation of aromatic compounds, and oxidative difunctionalization of 1,3-dienes. The catalytic cycles in these representative reactions feature re-oxidation of the palladium species with molecular oxygen as the terminal oxidant. Varying the combination of palladium catalyst and re-oxidant enables the formation of a variety of bonds through dehydrogenative cross-coupling reactions.

1 Introduction

2 Oxidative Amination of Terminal Alkenes

3 Direct Oxidative Arylation of Aromatic Compounds

4 Oxidative Silylation of Terminal Alkenes

5 Oxidative Difunctionalization of 1,3-Dienes

6 Conclusions and Perspectives

Key words

palladium - oxidative coupling - alkene - 1,3-diene - re-oxidation - aerobic oxidation

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