Brønsted Acid‐Catalyzed Cascade Reactions Involving 1,2‐Indole Migration |
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| Authors: | Estela Álvarez Dr. Olalla Nieto Faza Dr. Carlos Silva López Dr. Manuel A. Fernández‐Rodríguez Prof. Dr. Roberto Sanz |
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| Affiliation: | 1. área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Ba?uelos s/n, 09001‐Burgos (Spain);2. Departamento de Química Orgánica, Universidade de Vigo, Lagoas Marcosende, 36310‐Vigo, Galicia (Spain) |
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| Abstract: | A cascade reaction of indoles with propargylic diols involving an unprecedented metal‐free 1,2‐indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2‐migration and subsequent Nazarov cyclization. This Brønsted acid‐catalyzed protocol affords indole‐functionalized benzofulvene derivatives in high yields. |
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| Keywords: | benzofulvenes Brø nsted acid catalysis indole migration Nazarov cyclization |
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