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Synthesis 2012(6): 817-847  
DOI: 10.1055/s-0031-1289734
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Recent Developments in Palladium-Catalyzed Formation of Five- and Six-Membered Fused Heterocycles

K. C. Majumdar*a,b, Srikanta Samantaa, Biswajit Sinhaa
a Department of Chemistry, University of Kalyani, Kalyani 741235, India
Fax: +91(33)25828282; e-Mail: kcm_ku@yahoo.co.in;
b Department of Chemical Sciences, Tezpur University, Napaam, Tezpur 784 028, India
Further Information

Publication History

Received 23 December 2011
Publication Date:
01 March 2012 (online)

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Abstract

Palladium-mediated cyclization reactions have been recognized as some of the simplest and useful tools for regio- as well as stereoselective syntheses of carbo- and heterocyclic compounds. In the multi-step syntheses of natural products it is frequently used as one of the most important steps. In this review article, we have summarized the various ways of constructing five- and six-membered heterocyclic rings by palladium-catalyzed intramolecular cyclizations published between 2008 and 2010.

1 Introduction

2 Synthesis of Heterocycles via Alkene Cyclizations

2.1 Intramolecular Heck Cyclizations of Vinylic Halides

2.2 Intramolecular Heck Cyclizations of Aryl Halides

2.3 Intramolecular Heck Reactions of Aryl Triflates

2.4 Intramolecular Hydroxylations of Alkenes

2.5 Intramolecular Aminations of Alkenes

2.6 Intramolecular Annulations of Alkenes via Double C-H Activations

2.7 Intermolecular Annulations of Alkenes

3 Synthesis of Heterocycles via Alkyne Cyclizations

3.1 Intramolecular Cyclizations of Internal Alkynes

3.2 Intramolecular Cyclizations of Terminal Alkynes

3.3 Intermolecular Annulations of Alkynes

4 Synthesis of Heterocycles via Allene Cyclizations

5 Intramolecular Biaryl-Coupling Reactions

6.1 Biaryl Couplings via C-X Functionalizations

6.2 Biaryl Couplings via Double C-H Activations

6 Heterocycles via Carbonylative Cyclizations

7 Synthesis of Heterocycles from Alkane Substrates

8 Miscellaneous

9 Conclusion

Key words

palladium catalysis - fused heterocycles - C-H activation - C-C coupling - regioselectivity - stereoselectivity