Recent Advances in Transition-Metal-Catalyzed C–H Functionalization Reactions Involving Aza/Oxabicyclic Alkenes

Dedicated to Prof. Shinji Mura for his outstanding contributions to organic synthesis using transition-metal catalysis.

Abstract

Bicyclic alkenes, including oxa- and azabicyclic alkenes, readily undergo activation with facial selectivity in the presence of transition-metal complexes. This is due to the intrinsic angle strain on the carbon–carbon double bonds in such unsymmetrical bicyclic systems. During the past decades considerable progress has been made in the area of ring opening of bicyclic strained rings by employing the concept of C–H activation. This short review comprehensively compiles the various C–H bond activation assisted reactions of oxa- and azabicyclic alkenes, viz., ring-opening reactions, hydroarylation, and annulation reactions.

1 Introduction

2 Reactions of Heterobicyclic Ring Systems

2.1 Ring-Opening Reactions of Oxa- and Azabenzonorbornadienes

2.1.1 Reactions Using 7-Oxabenzonorbornadienes

2.1.2 Reactions Using 7-Azabenzonorbornadienes

2.2 Hydroarylation Reactions

2.3 Annulation Reactions

2.4 Other Reactions

3 Conclusion

Key words

C–H activation - bicyclic alkenes - 7-oxabenzonorbornadienes - 7-azabenzonorbornadienes - ring-opening - hydroarylation - annulation

Publication History

Received: 03 May 2021

Accepted after revision: 14 June 2021

Accepted Manuscript online:
14 June 2021

Article published online:
14 July 2021

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