Download PDF
Synthesis 2010(7): 1059-1074  
DOI: 10.1055/s-0029-1218669
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Thallium(III) in Organic Synthesis

Luiz F. Silva, Jr.*, Vânia M. T. Carneiro
Instituto de Química, Universidade de São Paulo, CP 26077, CEP 05513-970, São Paulo SP, Brazil
Fax: +55(11)38155579; e-Mail: luizfsjr@iq.usp.br;
Further Information

Publication History

Received 20 November 2009
Publication Date:
08 February 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

This review article discusses the literature regarding thallium(III) compounds in synthetic organic chemistry published in the last decade, including several applications in the total synthesis of natural products. The reactions that received the most attention in this period were: i) the oxidative rearrangement of chalcones; ii) the ring contraction of cyclic alkenes; iii) the oxidation of homoallylic alcohols; iv) aromatic thallations; and v) oxidative couplings, including with phenols.

1 Introduction

2 Non-Oxidative Reactions

3 Oxidative Reactions

3.1 Oxidations with Rearrangement

3.1.1 Ketones

3.1.1.1 Alkyl Aryl Ketones

3.1.1.2 Cyclic Ketones

3.1.1.3 Flavanones

3.1.1.4 Chalcones

3.1.2 Alkenes

3.1.3 Ring Opening of Cyclopropanes

3.2 Oxidations without Rearrangement

3.2.1 Cyclization Reactions

3.2.1.1 Alkenols

3.2.1.2 Carboxylic Acids

3.2.2 α-Oxidation of Ketones

3.2.3 Aromatic Thallation

3.2.4 Oxidative Coupling

3.2.4.1 Phenolic Oxidative Coupling

3.2.4.2 Non-Phenolic Oxidative Coupling

3.2.5 Oxidation of Phenols

3.2.6 Oxidation of Nitrogen Compounds

3.2.7 Disulfide Bond Formation

3.2.8 Deprotection of Thioketals

4 Miscellaneous

5 Conclusions

Key words

thallium(III) - rearrangement - coupling - cyclization - oxidation

1

The following alternative names for TTA are used in the literature: acetic acid thallium(3+) salt; thallium acetate; thallic acetate; thallic triacetate; thallium triacetate; thallium(III) triacetate; tris(acetato)thallium; tris(acetato-O)thallium.

2

The following alternative names for TTN are used in the literature: nitric acid, thallium(3+) salt; thallium nitrate; thallic nitrate; thallium nitrate; thallium trinitrate.

3

The following alternative names for TTFA are used in the literature: acetic acid, trifluoro-, thallium(3+) salt; thallic trifluoroacetate; thallium tris(trifluoroacetate); tris(trifluoroacetato)thallium.