Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives |
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| Authors: | Hashmi A Stephen K Rudolph Matthias Bats Jan W Frey Wolfgang Rominger Frank Oeser Thomas |
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| Institution: | 1. Organisch‐Chemisches Institut, Ruprecht‐Karls‐Universit?t, Heidelberg Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax (+49)?6221‐544205;2. Institut für Organische Chemie, Universit?t Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany);3. Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe‐Universit?t Frankfurt, Marie‐Curie‐Str. 11, 60439 Frankfurt (Germany);4. Crystallographic investigation. |
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| Abstract: | Different furans containing an ynamide or alkynyl ether moiety in the side chain were prepared. The gold-catalyzed transformation of these compounds delivered dihydroindole, dihydrobenzofuran, chroman, and tetrahydroquinoline derivatives at room temperature through very fast reactions. Furthermore, the stabilizing effect of the heteroatom directly attached to the intermediate arene oxides led to highly selective reactions, even in the case of only mono-substituted furans, which is quite different from previous results obtained with non-heteroatom-substituted alkynes. |
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| Keywords: | alkynes arenes gold heterocycles homogeneous catalysis |
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