Synlett 2019; 30(20): 2216-2232
DOI: 10.1055/s-0039-1690233
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© Georg Thieme Verlag Stuttgart · New York

Ionic Transfer Reactions with Cyclohexadiene-Based Surrogates

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J.C.L.W. gratefully acknowledges the Alexander von Humboldt Foundation for a Theodor Heuss fellowship (2018–2019). The research presented herein has been supported by the Deutsche Forschungsgemeinschaft (Grant No. Oe 249/11-1 and Oe 249/18-1) and the Cluster of Excellence Unifying Concepts in Catalysis (Grant No. EXC 314/2). M.O. is indebted to the Einstein Foundation Berlin for an endowed professorship.
Further Information

Publication History

Received: 20 September 2019

Accepted after revision: 14 October 2019

Publication Date:
06 November 2019 (online)

Abstract

A current research program in our laboratory is devoted to the development of cyclohexa-1,4-diene-based surrogates of difficult-to-handle compounds and their application in metal-free ionic transfer reactions. These investigations grew from our interest in silylium ion chemistry and consequently concentrated initially on surrogates of gaseous and explosive hydrosilanes such as Me3SiH and even monosilane (SiH4). Since then, we have expanded the concept to design surrogates of other species including H2, mineral acids (HI and HBr), and hydrocarbons (isobutane and isobutene). This Account summarizes our discoveries in this area to date, describing the challenges we faced along the way and how we combatted them.

1 Introduction

2 Transfer Hydrofunctionalization: Variation of the Electrofuge

3 Transfer Hydrofunctionalization: Variation of the Nucleofuge

4 Transfer Hydrohalogenation Using a Modified Surrogate

5 Surrogate Synthesis

6 Conclusion

 
  • References and Notes


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