Synthesis 2011(16): 2530-2539  
DOI: 10.1055/s-0030-1260122
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

On Gold-Mediated C-H Activation Processes

Teresa de Haro, Cristina Nevado*
Organic Chemistry Institute, University of Zürich, Winterthurerstr. 190, 8057 Zürich, Switzerland
Fax: +41(44)6356812; e-Mail: nevado@oci.uzh.ch;
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Publikationsverlauf

Received 20 May 2011
Publikationsdatum:
14. Juli 2011 (online)

Abstract

The ubiquitous nature of C-H bonds in organic molecules offers unparalleled opportunities for the development of more efficient methods to construct functionalized molecules. Recent advances in the developing area of gold-catalyzed C-H activation will be summarized here.

1 Introduction

2 Gold-Catalyzed Csp-H Activation Processes

2.1 Gold Acetylides as Nucleophiles

2.2 Gold Acetylides in Redox Processes

3 Gold-Catalyzed Csp²-H Activation Processes

3.1 Csp²-H Bond Activation by Gold(III)

3.2 Csp²-H Bond Activation by Gold(I)

4 Gold-Catalyzed Csp³-H Activation Processes

4.1 Csp³-H Activation by Gold-Carbene-Induced C-H Insertion

5 Conclusions

25

Dppf: 1,10-bis(diphenylphosphino)ferrocene.

36

An alternative mechanism in which gold acts as a Lewis acid activating the alkyne in the iodonium species triggering the attack of the heteroaromatic followed by β-elimination cannot be excluded.