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通过铑(III)催化的(杂)芳基与亚甲基氧杂环丁酮的 C-H 烯丙基化反应获得取代丙烯酸。

Access to Substituted Propenoic Acids via Rh(III)-Catalyzed C-H Allylation of (Hetero)Arenes with Methyleneoxetanones.

机构信息

Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, China.

University of Chinese Academy of Sciences , Beijing 100049, China.

出版信息

Org Lett. 2017 Nov 3;19(21):5972-5975. doi: 10.1021/acs.orglett.7b02983.

Abstract

An efficient synthesis of disubstituted acrylic acids has been realized via Rh(III)-catalyzed C-H activation of (hetero)arenes and coupling with four-membered methyleneoxetanones under redox-neutral conditions. In most cases, the reactions are silver-free, and the products are exclusively E-selective with a broad substrate scope. The transformation proceeds via ortho C-H activation followed by selective olefin insertion and β-oxygen elimination.

摘要

通过铑(III)催化的(杂)芳基 C-H 活化与四元亚甲基氧化丁内酯偶联,在氧化还原中性条件下实现了二取代丙烯酸的高效合成。在大多数情况下,反应无需银,产物具有广泛的底物范围,且为 E-选择性。该转化通过邻位 C-H 活化,然后进行选择性烯烃插入和β-氧消除。

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