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Synthesis 2005(2): 167-182
DOI: 10.1055/s-2005-861781
DOI: 10.1055/s-2005-861781
REVIEW
© Georg Thieme Verlag Stuttgart · New YorkTransition Metal-Catalyzed Hydroarylation of Alkynes
Further Information
Received
6 September 2004
Publication Date:
13 January 2005 (online)
Publication History
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.
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1 Introduction
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2 Reactions via Metal Vinylidenes
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2.1 Inter- and Intramolecular Reactions of Metal Vinylidenes with Arenes
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2.2 Electrocyclizations of Dienynes via Metal Vinylidenes
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3 Hydroarylation of Alkynes via π-Alkyne-Metal Complexes
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3.1 Intermolecular Hydroarylation of Alkynes Catalyzed by Metal Triflates
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3.2 Hydroarylation of Alkynes Catalyzed by Group 8-11 Metal Complexes
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3.2.1 Intermolecular Hydroarylation Catalyzed by Pd(II) and Pt(II)
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3.2.2 Intermolecular Hydroarylation Catalyzed by Au(III) and Au(I)
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3.2.3 Intramolecular Hydroarylation Catalyzed by Pd(0) or Pd(II)
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3.2.4 Intramolecular Hydroarylation of Alkynes with Ag(I)
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3.2.5 Intramolecular Hydroarylation Catalyzed by Pt(II), Pt(IV), Ru(II), and Other Metal Complexes
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3.3 Related Reactions Mediated by Protic Acids or Iodonium Cation
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4 Synthesis of Phenols by Metal-Catalyzed Reaction of Furans with Alkynes
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5 Summary and Outlook
Key words
cyclizations - hydroarylations - transition metals - electrophilic aromatic substitutions
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