Developments in Nitrosocarbonyl Chemistry: Mild Oxidation of N-Substituted Hydroxylamines Leads to New Discoveries

Abstract

This account describes the discovery and development of mild and efficient protocols for the generation of highly reactive nitroso compounds to allow their subsequent use in previously inaccessible or challenging chemistries.

1 Introduction

2 Formation of Nitrosocarbonyl Compounds

3 The Nitrosocarbonyl Ene Reaction

3.1 Single-Pot Nitrosocarbonyl Ene Reactions

3.2 Copper-Catalyzed Aerobic Oxidation for the Nitroso­carbonyl Ene Reaction

4 The Hetero-Diels–Alder Reaction as a Platform for Studying Aerobic Oxidation

5 Dual Catalysis and α-Functionalization Reactions

5.1 α-Amination Reaction of β-Keto Esters

5.2 α-Oxygenation Reaction of β-Keto Esters

6 The Future of Nitroso Chemistry

Key words

aerobic oxidation - nitroso - α-functionalization - electrophilic synthon - hydroxylamines

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