The Pauson-Khand Reaction –an Introduction - The Pauson-Khand Reaction - page 1

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The Pauson-Khand Reaction - an
Introduction

William J. Kerr

1.1 The Discovery and Early Evolution of the Khand Reaction 1

1.2 The Intermolecular Pauson-Khand Reaction 4

1.2.1 Regioselectivity of Alkyne Insertion 5

1.2.2 Regioselectivity of Alkene Insertion 6

1.3 The Intramolecular Pauson-Khand Reaction 8

1.4 Enhancing the Pauson-Khand Annulation by Reaction Promotion 9

1.4.1 Dry State Adsorption 9

1.4.2 Ultrasound Techniques 10

1.4.3 Microwave Promotion 10

1.4.4 Amine N -Oxide Additives 11

1.4.5 Sulfide Promoters 13

1.5 Catalytic Pauson-Khand Protocols 15

1.6 Concluding Remarks 16

Acknowledgements 17

References 17

1.1 The Discovery and Early Evolution of the Khand Reaction

Over the period from the 1950s, metal-mediated methods have changed the profile and
escalated the preparative potential of organic synthesis well beyond that which was previ-
ously possible or imaginable. New organic cyclisation techniques have been at the heart