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Sterically Controlled C−H Olefination of Heteroarenes

The regioselective functionalization of heteroarenes is a highly attractive synthetic target due to the prevalence of multiply substituted heteroarenes in nature and bioactive compounds. Some substitution patterns remain challenging: While highly efficient methods for the C2‐selective olefination of...

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Detalles Bibliográficos
Autores principales: Chen, Hao, Farizyan, Mirxan, Ghiringhelli, Francesca, van Gemmeren, Manuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384109/
https://www.ncbi.nlm.nih.gov/pubmed/32267990
http://dx.doi.org/10.1002/anie.202004521
Descripción
Sumario:The regioselective functionalization of heteroarenes is a highly attractive synthetic target due to the prevalence of multiply substituted heteroarenes in nature and bioactive compounds. Some substitution patterns remain challenging: While highly efficient methods for the C2‐selective olefination of 3‐substituted five‐membered heteroarenes have been reported, analogous methods to access the 5‐olefinated products have remained limited by poor regioselectivities and/or the requirement to use an excess of the valuable heteroarene starting material. Herein we report a sterically controlled C−H olefination using heteroarenes as the limiting reagent. The method enables the highly C5‐selective olefination of a wide range of heteroarenes and is shown to be useful in the context of late‐stage functionalization.