Activation of C–F, Si–F, and S–F Bonds by N-Heterocyclic Carbenes and Their Isoelectronic Analogues

Ewa Pietrasiak; Eunsung Lee

doi:10.1055/s-0040-1707106

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(14): 1349-1360
DOI: 10.1055/s-0040-1707106

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Activation of C–F, Si–F, and S–F Bonds by N-Heterocyclic Carbenes and Their Isoelectronic Analogues

Ewa Pietrasiak

^aDepartment of Chemistry, Pohang University of Science and Technology, Pohang, 37673, South Korea

,

Eunsung Lee∗

^aDepartment of Chemistry, Pohang University of Science and Technology, Pohang, 37673, South Korea

^bDivision of Advanced Materials Science, Pohang University of Science and Technology, Pohang 37673, South Korea eMail: eslee@postech.ac.kr

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Abstract

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Abstract

Reactions involving C–F, Si–F, and S–F bond cleavage with N-heterocyclic carbenes and isoelectronic species are reviewed. Most examples involve activation of aromatic C–F bond via an S_NAr pathway and nucleophilic substitution of fluorine in electron-deficient olefins. The mechanism of the C–F bond activation depends on the reaction partners and the reaction can proceed via addition–elimination, oxidative addition (concerted or stepwise) or metathesis. The adducts formed upon substitution find applications in organic synthesis, as ligands and as stable radical precursors, but in most cases, their full potential remains unexplored.

1 Introduction

1.1 The C–F Bond

1.2 C–F Bond Activation: A Short Summary

1.3 C–F Bond Activation: A Special Case of S_NAr

1.4 N-Heterocyclic Carbenes (NHCs)

1.5 The Purpose of this Article

2 C–F bond Activation in Acyl Fluorides

3 Activation of Vinylic C–F Bonds

4 Activation of Aromatic C–F Bonds

5 X–F Bond Activation (X = S or Si)

6 C–F Bond Activation by Main Group Compounds Isoelectronic with NHCs

7 Conclusions and Outlook

Key words

NHC - fluorine - carbon–fluorine - nucleophilic substitution - main group elements

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Referenzen

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