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Synlett 2019; 30(20): 2216-2232
DOI: 10.1055/s-0039-1690233
DOI: 10.1055/s-0039-1690233
account
Ionic Transfer Reactions with Cyclohexadiene-Based Surrogates
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.Weitere Informationen
Publikationsverlauf
Received: 20. September 2019
Accepted after revision: 14. Oktober 2019
Publikationsdatum:
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
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For our contributions to this area in the form of review articles, see:
For the seminal report, see:
For the subsequent comments, see:
For a review, see:
For selected examples of original work, see:
For the seminal description of this approach, see:
For a systematic study of the synthesis of various Me3Si+(arene) complexes, see:
For general reviews of chemistry mediated by B(C6F5)3 and related Lewis acids, see:
For an overview of hydrosilylation chemistry, see:
For the related radical transfer hydrosilylation, see:
For reviews of the use of organogermanium compounds, see:
For previous examples of the use of cyclohexa-1,4-diene in gallium(III)-catalyzed transfer hydrogenation, see:
These intermediates have previously been invoked in B(C6F5)3-catalyzed imine hydrogenation with dihydrogen, see:
For seminal reports of B(C6F5)3-catalyzed alkene hydrogenation with dihydrogen, see:
For previous isolated examples of transfer hydro-tert-butylation, see:
Cyclohexa-1,4-dienes bearing formally nucleofugal amide groups have previously been prepared, although as these reactions proceed under radical conditions the products have the opposite regioselectivity to that that would be expected under Lewis acidic conditions. For details, see:
For examples, see:
Cyclohexa-1,4-dienes bearing formally nucleofugal hydrocarbon groups have previously been prepared and used in a limited number of hydroalkylation reactions, although as these proceed under radical conditions the products have the opposite regioselectivity. For details, see:
For previous example of HX surrogates, see:
For an early example, see:
This process has also been reported in the patent literature, see:
For early work on the silylation of 9,10-dihydroanthracene, see: