Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 2120-2128Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.249
Keywords
alkyne; chromene; gold; gold catalysis; hydroarylation; iodine
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Funding
- Spanish MINECO and the Principality of Asturias [FC-11CO11-17, CTQ2010-20517-C02-01]
- Spanish Goverment for a FPU predoctoral fellowship
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An efficient entry to the preparation of elusive 4-unsubstituted-3-iodo-2H-chromenes has been accomplished as result of a catalytic cyclization. Thus, upon exposition of [(3-iodoprop-2-yn-1-yl) oxy] arenes to IPrAuNTf2 (3 mol %), in 1,4-dioxane at 100 degrees C, the desired heterocyclic motif is readily assembled. This process nicely tolerates a variety of functional groups and, interestingly, it is compatible with the presence of strong electron-withdrawing groups attached to the arene. The overall transformation can be termed as a new example of a migratory cycloisomerization and, formally, it involves well-blended 1,2-iodine shift and hydroarylation steps.
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