Indium-promoted butenolide synthesis through consecutive C-C and C-O bond formations in aqueous tetrahydrofuran enabled by radicals
An indium-promoted lactonization of (indol-3-yl)-2-oxoacetaldehydes, which allows the synthesis of substituted γ-methylenebutenolides in an aqueous environment, has been accomplished. This process is in clear contrast with the established metal-mediated reactivity of unsaturated organic halides and...
| Authors: | , , , , |
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| Format: | article |
| Status: | Published version |
| Publication Date: | 2023 |
| Country: | España |
| Institution: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repository: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/311751 |
| Online Access: | http://hdl.handle.net/10261/311751 |
| Access Level: | Open access |
| Summary: | An indium-promoted lactonization of (indol-3-yl)-2-oxoacetaldehydes, which allows the synthesis of substituted γ-methylenebutenolides in an aqueous environment, has been accomplished. This process is in clear contrast with the established metal-mediated reactivity of unsaturated organic halides and carbonyls. The use of an aqueous medium and the facile purification profile make our protocol a convenient and sustainable synthetic strategy. A plausible reaction pathway has been proposed with the help of density functional theory calculations. |
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