2019
DOI: 10.26434/chemrxiv.10099058
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Sterically Controlled C‒H Olefination of Heteroarenes

Abstract: 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.<br>

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“…As expected on the basis of related transformations and our mechanistic data, the reactions proceed with a mixture of steric and electronic control, providing access to the desired products in moderate to good yields. Importantly, on the basis of literature studies, 9a c , 10 11 12 individual yields could probably be increased substantially by fine-tuning the reaction conditions. In this study we provide evidence that our protocol can be used to introduce olefins into complex molecular scaffolds.…”
mentioning
confidence: 99%
“…As expected on the basis of related transformations and our mechanistic data, the reactions proceed with a mixture of steric and electronic control, providing access to the desired products in moderate to good yields. Importantly, on the basis of literature studies, 9a c , 10 11 12 individual yields could probably be increased substantially by fine-tuning the reaction conditions. In this study we provide evidence that our protocol can be used to introduce olefins into complex molecular scaffolds.…”
mentioning
confidence: 99%