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Beilstein J Org Chem. 2013 Oct 16;9:2120-8. doi: 10.3762/bjoc.9.249. eCollection 2013.

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives.

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Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, C/Julián Clavería 8, Oviedo, 33006, Spain.


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 °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.


alkyne; chromene; gold; gold catalysis; hydroarylation; iodine

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