Synthesis 2003(5): 0633-0655
DOI: 10.1055/s-2003-38064
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Indium in Organic Synthesis

Joachim Podlech*, Thomas C. Maier
Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Fax: +49(711)6854269; e-Mail: joachim.podlech@po.uni-stuttgart.de;
Further Information

Publication History

Received 20 January 2003
Publication Date:
21 March 2003 (online)

Abstract

The various applications of indium in organic synthesis are highlighted in this review. Major fields are Barbier-type reactions, especially allyl additions to carbonyl compounds, and Reformatsky reactions. Special emphasis is placed on reactions, which have been examined only recently, i.e. reductions of various functionalities, indium-catalyzed reactions and palladium/indium-mediated reactions.

  • 1 Introduction

  • 2 Barbier-Type Reactions

  • 2.1 Indium-Mediated Additions to Aldehydes and Ketones

  • 2.2 The Role of the Allyl Halide

  • 2.3 Diastereoselectivity

  • 2.4 Regioselectivity

  • 2.5 Enantioselectivity

  • 2.6 Indium-Mediated Additions to Further Carbonyl Derivatives

  • 2.7 Indium-Mediated Additions to C-C Multiple Bonds

  • 2.8 Reaction of Non-Allylic Substrates in Barbier-Type Reactions

  • 3 Palladium-Catalyzed Allylic Substitutions and Cross-Couplings of Indium Intermediates

  • 4 Reformatsky-Type Reactions

  • 5 Indium-Catalyzed Reactions

  • 6 Nucleophilic Substitutions Using Intermediate Allylindium Compounds

  • 7 Allylindium Reagents

  • 8 Indium-Mediated Reductions

  • 8.1 Reduction and Deoxygenation of N-Containing Functionalities

  • 8.2 Reductive Dehalogenations

  • 8.3 Reduction of Carbonyl Groups

  • 8.4 Miscellaneous Reductions

  • 9 Conclusion

68

Podlech, J. unpublished results.

134

Steurer, S.; Podlech, J. unpublished results.