Radical-type Reactions Controlled by Cobalt: From Carbene Radical Reactivity to the Catalytic Intermediacy of Reactive o-Quinodimethanes

Colet te Grotenhuis; Bas de Bruin

doi:10.1055/s-0037-1610204

Synlett, Table of Contents

Synlett 2018; 29(17): 2238-2250
DOI: 10.1055/s-0037-1610204

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Radical-type Reactions Controlled by Cobalt: From Carbene Radical Reactivity to the Catalytic Intermediacy of Reactive o-Quinodimethanes

Colet te Grotenhuis

Homogeneous, Supramolecular and Bio-Inspired Catalysis (HomKat) group, Van ’t Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam (UvA), Science Park 904, 1098 XH Amsterdam, The Netherlands Email: b.debruin@uva.nl

,

Bas de Bruin *

Homogeneous, Supramolecular and Bio-Inspired Catalysis (HomKat) group, Van ’t Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam (UvA), Science Park 904, 1098 XH Amsterdam, The Netherlands Email: b.debruin@uva.nl

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Abstract

All articles of this category

Dedicated to Professor Michael P. Doyle, in recognition of hisexcellent contributions to the field of metallo-carbene chemistry.

Abstract

In this account, we summarize our recent efforts in the fields of ‘open-shell organometallic chemistry’ and ‘metalloradical catalysis’. We focus in particular on the use of so-called ‘carbene radicals’ for the synthesis of a variety of useful synthons for organic chemistry. We further show that unexpected reactivity arises from catalytic synthesis of unusual o-quinone methide and o-quinodimethane intermediates that undergo subsequent rearrangements to uncommon products.

1 Introduction

2 General (Fischer-Type) Carbene and Nitrene Reactivity and Their Relation to Carbene and Nitrene Radical Reactivity

3 Carbene and Nitrene (Radical) Precursors

4 Formation and Intrinsic Radical-Type Reactivity of Carbene and Nitrene Radicals

5 Types of Cobalt Catalysts Used in Reactions Involving Carbene and Nitrene Radicals

6 Applications of Cobalt-Catalyzed Ring-Closure Reactions via Carbene Radicals

7 Intermediacy of o-Quinone Methide and o-Quidodimethanes in Carbene Ring-Closing Reactions

8 Conclusion

Key words

carbene radicals - carbene reactivity - metalloradical catalysis - o-quinodimethanes - open-shell organometallic chemistry

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References

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