A General Synthesis of Alkenyl‐Substituted Benzofurans,Indoles, and Isoquinolones by Cascade Palladium‐Catalyzed Heterocyclization/Oxidative Heck Coupling |
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| Authors: | Dr Rosana Álvarez Claudio Martínez Youssef Madich J Gabriel Denis Dr José M Aurrecoechea Prof?Dr Ángel R de?Lera |
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| Institution: | 1. Departamento de Química Orgánica, Facultad de Química, Universidade de Vigo, Lagoas Marcosende, 36310 Vigo (Spain), Fax: (+34)?986‐811940;2. Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080 Bilbao (Spain), Fax: (+34)?946‐013500 |
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| Abstract: | Structurally diverse C3‐alkenylbenzofurans, C3‐alkenylindoles, and C4‐alkenylisoquinolones are efficiently prepared by using consecutive Sonogashira and cascade Pd‐catalyzed heterocyclization/oxidative Heck couplings from readily available ortho‐iodosubstituted phenol, aniline, and benzamide substrates, alkynes, and functionalized olefins. The cyclization of O‐ and N‐heteronucleophiles follows regioselective 5‐endo‐dig‐ or 6‐endo‐dig‐cyclization modes, whereas the subsequent Heck‐type coupling with both mono‐ and disubstituted olefins takes place stereoselectively with exclusive formation of the E isomers in most cases. |
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| Keywords: | cyclization Heck reaction heterocycles homogeneous catalysis palladium |
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