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