钯催化[60]富勒烯与芳基化合物的反应：通过烯醇盐介导的 sp C-H 键活化和羟化反应。

Palladium-Catalyzed Reaction of [60]Fullerene with Aroyl Compounds via Enolate-Mediated sp C-H Bond Activation and Hydroxylation.

机构信息

State Key Laboratory Cultivation Base for Nonmetal Composites and Functional Materials, Southwest University of Science and Technology , Mianyang, Sichuan 621010, P. R. China.

Department of Chemistry, School of Materials Science and Engineering, Southwest University of Science and Technology , Mianyang 621010, China.

出版信息

J Org Chem. 2018 Jan 19;83(2):672-683. doi: 10.1021/acs.joc.7b02620. Epub 2018 Jan 10.

DOI:10.1021/acs.joc.7b02620

PMID:29264916

Abstract

A convenient and highly efficient palladium-catalyzed reaction of [60]fullerene (C) with aroyl compounds via enolate-mediated C-H activation and hydroxylation has been exploited for the first time to synthesize novel C-fused dihydrofurans, and rare 1,4-fullerenols. Further functionalization including etherification, and esterification of synthesized 1,4-fullerenols provided efficient access to versatile fullerene derivatives. Moreover, a plausible reaction mechanism leading to the observed products is proposed.

摘要

首次利用[60]富勒烯（C）与芳基化合物通过烯醇化物介导的 C-H 活化和羟化的方便且高效的钯催化反应，合成了新型的 C 稠合二氢呋喃和罕见的 1,4-富勒醇。进一步的官能化，包括合成的 1,4-富勒醇的醚化和酯化，为多功能富勒烯衍生物提供了有效的途径。此外，提出了一种合理的反应机理，解释了观察到的产物的形成。