Transition Metal-Catalyzed Hydroarylation of Alkynes

Cristina Nevado; Antonio M. Echavarren

doi:10.1055/s-2005-861781

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Synthesis 2005(2): 167-182
DOI: 10.1055/s-2005-861781

REVIEW

Transition Metal-Catalyzed Hydroarylation of Alkynes

Cristina Nevado, Antonio M. Echavarren*
Institute of Chemical Research of Catalonia (ICIQ), 43007 Tarragona and Departamento de Química Orgánica, Universidad Autónoma de Madrid (UAM), 28049 Madrid, Spain
Fax: +34(977)920225; e-Mail: aechavarren@iciq.es;

Further Information

Publication History

Received 6 September 2004
Publication Date:
13 January 2005 (online)

Abstract
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Abstract

The different methods for the hydroarylation of alkynes (also known simply as arylation of alkynes or alkenylation of arenes) catalyzed by transition metals are presented as a function of the proposed mechanisms. Related iodonium-promoted and protic acid-catalyzed cyclizations of alkynyl arenes are also reviewed.

1 Introduction
2 Reactions via Metal Vinylidenes
2.1 Inter- and Intramolecular Reactions of Metal Vinylidenes with Arenes
2.2 Electrocyclizations of Dienynes via Metal Vinylidenes
3 Hydroarylation of Alkynes via π-Alkyne-Metal Complexes
3.1 Intermolecular Hydroarylation of Alkynes Catalyzed by Metal Triflates
3.2 Hydroarylation of Alkynes Catalyzed by Group 8-11 Metal Complexes
3.2.1 Intermolecular Hydroarylation Catalyzed by Pd(II) and Pt(II)
3.2.2 Intermolecular Hydroarylation Catalyzed by Au(III) and Au(I)
3.2.3 Intramolecular Hydroarylation Catalyzed by Pd(0) or Pd(II)
3.2.4 Intramolecular Hydroarylation of Alkynes with Ag(I)
3.2.5 Intramolecular Hydroarylation Catalyzed by Pt(II), Pt(IV), Ru(II), and Other Metal Complexes
3.3 Related Reactions Mediated by Protic Acids or Iodonium Cation
4 Synthesis of Phenols by Metal-Catalyzed Reaction of Furans with Alkynes
5 Summary and Outlook

Key words

cyclizations - hydroarylations - transition metals - electrophilic aromatic substitutions

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