Norbornene in Organic Synthesis

Dedicated to Prof. Kang Zhao on the occasion of his 60^th birthday

Abstract

The norbornene skeleton possesses an alkene functionality with a fixed conformation, and represents unique reactivity. The use of norbornene and analogues as substrates is overviewed; reactivities are discussed as well as the role of norbornenes as ligands assisting modern organic transformations.

1 Introduction

2 Synthesis of Substituted Norbornenes

2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions

2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed­ Reaction Conditions

2.3 Alkylation of Norbornene

2.4 Multistep Synthesis

3 Synthesis of Substituted Norbornanes

3.1 Three-Membered-Ring Formation

3.2 Formation of Four-Membered Rings

3.3 Five- and Six-Membered Ring Formation

3.4 Syntheses of Difunctionalized Norbornanes

4 Synthesis of Cyclopentanes

4.1 Oxidation Reactions

4.2 Ring-Opening Cross Metathesis (ROCM)

4.3 Ring-Opening Metathesis Polymerization (ROMP)

4.4 Palladium-Catalyzed Ring-Opening of Norbornene

5 Norbornene-Mediated Reactions

5.1 Palladium Insertion into Carbon–Halide Bonds

5.2 Palladium Insertion into N–H and C–H Bonds

5.3 Norbornene as Ligand in Mediated Reactions

6 Conclusion

Key words

norbornene - C–H activation - norbornane - ring-opening metathesis

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