Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1λ3,2-benziodoxol-3(1H)-one and Alkynylation of Indoles, Thiophenes, and Anilines

Jonathan P. Brand; Jérôme Waser

doi:10.1055/s-0031-1290589

Synthesis, Table of Contents

Synthesis 2012; 44(8): 1155-1158
DOI: 10.1055/s-0031-1290589

special topic

Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1λ³,2-benziodoxol-3(1H)-one and Alkynylation of Indoles, Thiophenes, and Anilines

Authors

Jonathan P. Brand

Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland, Fax: +41(21)69397 00 Email: jerome.waser@epfl.ch
Jérôme Waser*

Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland, Fax: +41(21)69397 00 Email: jerome.waser@epfl.ch

Abstract

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Abstract

An efficient procedure was developed for the synthesis of 1-[(triisopropylsilyl)ethynyl]-1λ³,2-benziodoxol-3(1H)-one on a 100-mmol (36-g) scale. The benziodoxolone can be used for the gold-catalyzed direct alkynylation of indole, 2-hexylthiophene, or N,N-dibenzylaniline on a 5- to 10-mmol scale.

Key words

alkynes - arenes - catalysis - heterocycles - iodine

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References

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