Oxidative Alkane C−H Alkoxycarbonylation |
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Authors: | Lijun Lu Renyi Shi Luyao Liu Jingwen Yan Fangling Lu Prof. Aiwen Lei |
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Affiliation: | 1. College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, Wuhan, P. R. China;2. National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, P. R. China |
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Abstract: | Directly utilizing a chemical feedstock to construct valuable compounds is an attractive prospect in organic synthesis. In particular, the combination of C(sp3)?H activation and oxidative carbonylation involving alkanes and CO gas is a promising and efficient method to synthesize carbonyl derivatives. However, due to the high C?H bond dissociation energy and low polarity of unactivated alkanes, the carbonylation of unactivated C(sp3)?H bonds still remains a great challenge. In this work, we introduce a palladium‐catalyzed radical oxidative alkoxycarbonylation of alkanes to prepare numerous alkyl carboxylates. Various alkanes and alcohols were compatible, generating the desired products in up to 94 % yield. Remarkably, ethane, a constituent of natural gas, could be employed as a substrate under the standard reaction conditions. Preliminary mechanistic studies revealed a probable palladium‐catalyzed radical process. |
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Keywords: | alkanes carbonylation C− H activation palladium radical reactions |
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