Download PDF
Synthesis 2010(24): 4131-4153  
DOI: 10.1055/s-0030-1258262
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Alkenylation Reactions of Heteroarenes by Transition-Metal Catalysts

Renzo Rossi*, Fabio Bellina*, Marco Lessi
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, 56126 Pisa, Italy
Fax: +39(050)2219260; e-Mail: rossi@dcci.unipi.it; e-Mail: bellina@dcci.unipi.it;
Further Information

Publication History

Received 20 July 2010
Publication Date:
22 September 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

This review with 272 references covers the literature published up to the end of February 2010 on the methods, other than the Mizoroki-Heck reaction, that have been developed in the last three decades to introduce carbon-carbon double bonds, frequently even in a stereocontrolled manner, onto heteroarene moieties by using transition-metal-catalyzed reactions that do not involve the use of stoichiometric amounts of organometallic reagents. The practicality and versatility of these methods with respect to substrate scope and operational costs are discussed.

1 Introduction

2 N-Alkenylation Reactions of Free (NH)-Azoles with Alkenyl­ Halides or Pseudohalides

3 Direct C-Alkenylation Reactions of Heteroarenes with Alkenyl­ Halides, Triflates, Phosphates, and 1,3-Dicarbonyl Compounds

4 Oxidative Coupling Reactions of Heteroarene C(sp²)-H Bonds with Alkenes and Decarboxylative Alkenylation Reactions­ of Heteroarenecarboxylic Acids with Alkenes

5 Addition of Heteroarene C(sp²)-H Bonds to Alkynes

6 Heteroarylcyanation of Alkynes

7 Conclusions

Key words

catalysis - transition metals - heteroarenes - olefination - coupling