Oxidative Alkane C−H Alkoxycarbonylation
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- 作者：Lijun Lu ; Renyi Shi ; Luyao Liu ; Jingwen Yan ; Fangling Lu and Prof. Aiwen Lei
- 刊名：Chemistry - A European Journal
- 出版年：2016
- 出版时间：October 4, 2016
- 年：2016
- 卷：22
- 期：41
- 页码：14484-14488
- 全文大小：1540K
- ISSN：1521-3765
文摘
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.