钯催化[60]富勒烯与 2-芳基环状 1,3-二羰基化合物氧化环加成合成[60]富勒烯稠合螺吲哚。

Synthesis of [60]Fullerene-Fused Spiroindanes by Palladium-Catalyzed Oxidative Annulation of [60]Fullerene with 2-Aryl Cyclic 1,3-Dicarbonyl Compounds.

机构信息

CAS Key Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Hefei National Laboratory for Physical Sciences at Microscale, and Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, P. R. China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou, Gansu 730000, P. R. China.

出版信息

Org Lett. 2016 Jun 3;18(11):2616-9. doi: 10.1021/acs.orglett.6b01043. Epub 2016 May 18.

DOI:10.1021/acs.orglett.6b01043

PMID:27192615

Abstract

A convenient and facile palladium-catalyzed reaction of [60]fullerene (C60) with 2-aryl cyclic 1,3-dicarbonyl compounds via the enolate-directed sp(2) C-H activation and sp(3) C-H functionalization has been exploited to synthesize the novel and rare C60-fused spiroindanes for the first time. This reaction is easy to perform with broad substrate scope and provides diversified products in 20-50% yields. A plausible reaction mechanism involving the palladium-catalyzed enolate-directed C-H activation and subsequent cyclization has been proposed, and the electrochemistry of the C60-fused spiroindanes has also been investigated.

摘要

通过烯醇化物导向的 sp(2) C-H 活化和 sp(3) C-H 官能化，实现了一种方便、简易的钯催化[60]富勒烯（C60）与 2-芳基环状 1,3-二羰基化合物的反应，首次合成了新型罕见的 C60 稠合螺吲哚类化合物。该反应具有广泛的底物范围，易于操作，以 20-50%的产率提供了多样化的产物。提出了一个合理的反应机理，涉及钯催化的烯醇化物导向的 C-H 活化和随后的环化，还研究了 C60 稠合螺吲哚的电化学。