Thallium in Organic Synthesis. Xxii. Electrophilic Aromatic Thallation Using Thallium (III) Trifluoroacetate. A Simple Synthesis of Aromatic Iodides

Alexander Mckillop; John D. Hunt; Michael J. Zelesko; Joanna S. Fowler; Edward C. Taylor; George Mcgillivray; Frank Kienzle

doi:10.1021/ja00748a029

Thallium in Organic Synthesis. Xxii. Electrophilic Aromatic Thallation Using Thallium (III) Trifluoroacetate. A Simple Synthesis of Aromatic Iodides

Alexander Mckillop, John D. Hunt, Michael J. Zelesko, Joanna S. Fowler, Edward C. Taylor, George Mcgillivray, Frank Kienzle

Research output: Contribution to journal › Article › peer-review

159 Scopus citations

Abstract

The preparation of thallium(III) trifluoroacetate and its efficacy as a reagent for electrophilic aromatic thallation are described. Arylthallium ditrifluoroacetates, the products of thallation, react rapidly with aqueous potassium iodide to produce thallium(I) iodide and the corresponding aromatic iodide. This extremely simple synthesis of aromatic iodides is generally applicable to a wide range of aromatic and heterocyclic substrates.

Original language	English
Pages (from-to)	4841-4844
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	93
Issue number	19
DOIs	https://doi.org/10.1021/ja00748a029
State	Published - 1 Sep 1971
Externally published	Yes

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abstract = "The preparation of thallium(III) trifluoroacetate and its efficacy as a reagent for electrophilic aromatic thallation are described. Arylthallium ditrifluoroacetates, the products of thallation, react rapidly with aqueous potassium iodide to produce thallium(I) iodide and the corresponding aromatic iodide. This extremely simple synthesis of aromatic iodides is generally applicable to a wide range of aromatic and heterocyclic substrates.",

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Thallium in Organic Synthesis. Xxii. Electrophilic Aromatic Thallation Using Thallium (III) Trifluoroacetate. A Simple Synthesis of Aromatic Iodides. / Mckillop, Alexander; Hunt, John D.; Zelesko, Michael J. et al.
In: Journal of the American Chemical Society, Vol. 93, No. 19, 01.09.1971, p. 4841-4844.

Research output: Contribution to journal › Article › peer-review

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AU - Zelesko, Michael J.

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AU - Mcgillivray, George

AU - Kienzle, Frank

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Thallium in Organic Synthesis. Xxii. Electrophilic Aromatic Thallation Using Thallium (III) Trifluoroacetate. A Simple Synthesis of Aromatic Iodides

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