Synthesis 2012; 44(8): 1155-1158
DOI: 10.1055/s-0031-1290589
special topic
© Georg Thieme Verlag Stuttgart · New York

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

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
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Publikationsverlauf

Received: 19. Januar 2012

Accepted after revision: 24. Februar 2012

Publikationsdatum:
22. März 2012 (online)

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.

 
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