Carbonylated Indoles from Pd^II-Catalyzed Intermolecular Reactions of Indolyl Cores

Abstract

This review summarizes palladium-catalyzed carbonylation, transmetalation, and cross-coupling reactions that lead to carbonylated indoles from indoles and indolyl compounds. Special attention is drawn to procedures involving the C(sp²)–H substitution of free (NH)-indoles or (N-substituted)-indoles. Proposed mechanisms are described with, in some cases, personal comments.

1 Introduction

2 Carbonylative Reactions

2.1 Indolyl Halides as Starting Substrates

2.2 Indolyl Iodides as Intermediates

2.3 Indolylborates as Intermediates

2.4 C(sp²)–H Reactions

2.4.1 Carboxylation

2.4.2 Carbonylative Alkoxylation

2.4.3 Carbonylative Arylation

2.4.4 Carbonylative Alkenylation

2.4.5 Carbonylative Alkylation

2.4.6 Double Carbonylation

3 Cross-Coupling of Stannyl- or Mercurioindoles

4 Cross-Coupling of Indoles

4.1 Aldehydes

4.2 Alcohols

4.3 α-Diketones

4.4 α-Oxo Esters

4.5 α-Oxocarboxylic Acids

4.6 Nitriles

4.7 Isocyanides

4.8 Isothiocyanates and Isocyanates

4.9 α-Aminocarbonyl Compounds

4.10 Vinyl Ethers or Vinyl Amides

4.11 Toluene and Substituted Toluenes

4.12 Bromodichloromethane

5 Conclusion

Key words

acylation - carbonylation - palladium - catalysis - indoles

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