Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

Dedicated to Prof. Dr. Henning Hopf

Abstract

The remarkable structural and electronic properties of rigid non-conjugated hydrocarbons afford attractive opportunities to design molecular building blocks for both medicinal and material applications. The bridgehead positions provide the possibility to append diverse functional groups at specific angles and in specific orientations. The current review summarizes the synthetic development in CH functionalization of three rigid scaffolds namely: (a) cubane, (b) bicyclo[1.1.1]pentane (BCP), (c) adamantane.

1 Introduction

2 Cubane

2.1 Cubane Synthesis

2.2 Cubane Functionalization

3 Bicyclo[1.1.1]pentane (BCP)

3.1 BCP Synthesis

3.2 BCP Functionalization

4 Adamantane

4.1 Adamantane Synthesis

4.2 Adamantane Functionalization

5 Conclusions and Outlook

Key words

cubane - bicyclo[1.1.1]pentane - adamantane - rigid scaffolds - CH-functionalization

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