N-heterocyclic carbene-copper(I) complexes in homogeneous catalysis

Silvia Diez-Gonzalez, Steven Patrick Nolan

Research output: Contribution to journalReview articlepeer-review

Abstract

N-Heterocyclic carbenes (NHCs) have become increasingly popular as ligands for transition metals, thanks to their remarkable successes in metathesis and cross-coupling areas. Important advances have also been achieved in organocopper chemistry. To date, the reported neutral N-heterocyclic carbene-copper(I) complexes have shown outstanding catalytic activity. In this account, we describe the application of such complexes in a variety of organic transformations.

1 Introduction

2 Copper-Hydride-Mediated Reactions

2.1 Reduction of Carbonyl Compounds

2.1.1 Activity and Scope

2.1.2 Mechanistic Considerations

2.2 Related Transformations

3 Carbene Transfer Reactions

3.1 Cyclopropanation and Insertion Reactions

3.2 Olefination Reactions

4 [3+2] Cycloaddition of Azides and Alkynes

4.1 'Click Chemistry'

4.2 Use of Internal Alkynes: Mechanistic Implications

5 Miscellaneous Reactions

6 Concluding Remarks.

Original languageEnglish
Pages (from-to)2158-2167
Number of pages10
JournalSynlett
Issue number14
DOIs
Publication statusPublished - 3 Sept 2007

Keywords

  • N-heterocyclic carbene
  • copper
  • diazo compounds
  • homogeneous catalysis
  • hydrosilylation
  • REDUCTIVE ALDOL REACTION
  • QUATERNARY STEREOGENIC CENTERS
  • CARBENE COPPER(I) COMPLEXES
  • AZIDE-ALKYNE CYCLOADDITION
  • ONE-POT SYNTHESIS
  • CONJUGATE REDUCTION
  • CARBONYL-COMPOUNDS
  • ENANTIOSELECTIVE SYNTHESIS
  • ASYMMETRIC-SYNTHESIS
  • ETHYL DIAZOACETATE

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