Indium in Organic Synthesis

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

indium - allyl addition - Barbier reaction - Reformatsky reaction - reductions

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