Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 1763-1767Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.204
Keywords
alkynylation; benzofurans; cooperative catalysis; direct functionalization; gold catalysis; hypervalent iodine
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Funding
- EPFL
- F. Hoffmann-La Roche Ltd
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The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynylation of benzofurans substituted with alkyl, aryl, halogen and ether groups. The reaction was also successful in the case of the more complex drug 8-methoxypsoralen (8-MOP).
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