Synthesis 2005(2): 167-182  
DOI: 10.1055/s-2005-861781
REVIEW
© Georg Thieme Verlag Stuttgart · New York

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

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