Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine‐Directed para and ortho C−H Functionalization
Among halogenated aromatics, iodoarenes are unique in their ability to produce the bench-stable halogen(III) form. Earlier, such iodine(III) centers were shown to enable C−H functionalization ortho to iodine via halogen-centered rearrangement. The broader implications of this phenomenon are explored...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2019 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/202237 |
| Acceso en línea: | http://hdl.handle.net/10261/202237 |
| Access Level: | acceso abierto |
| Palabra clave: | C−C coupling C−H functionalization Hypervalent iodine Iterative methods Oxidative coupling |
| Sumario: | Among halogenated aromatics, iodoarenes are unique in their ability to produce the bench-stable halogen(III) form. Earlier, such iodine(III) centers were shown to enable C−H functionalization ortho to iodine via halogen-centered rearrangement. The broader implications of this phenomenon are explored by testing the extent of an unusual iodane-directed para C−H benzylation, as well as by developing an efficient C−H coupling with sulfonyl-substituted allylic silanes. Through the combination of the one-shot nature of the coupling event and the iodine retention, multisubstituted arenes can be prepared by sequentially engaging up to three aromatic C−H sites. This type of iodine-based iterative synthesis will serve as a tool for the formation of value-added aromatic cores. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
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