Sterically Controlled C−H Olefination of Heteroarenes
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Authors: | Hao Chen Mirxan Farizyan Francesca Ghiringhelli Manuel van Gemmeren |
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Abstract: | 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. |
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Keywords: | C− H activation Fujiwara– Moritani reaction heteroarenes olefination palladium |
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