Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis

被引：44

作者：

Garnier, Tony ^{[1
]}

Danel, Mathieu ^{[1
]}

Magne, Valentin ^{[1
]}

Pujol, Anthony ^{[1
]}

Beneteau, Valerie ^{[2
]}

Pale, Patrick ^{[2
]}

Chassaing, Stefan ^{[1
,2
]}

机构：

[1] Univ Toulouse, CNRS, ITAV, Toulouse, France

[2] Univ Strasbourg, CNRS UMR7177, Inst Chim, Lab Synthese Reactivite Organ & Catalyse LASYROC, 4 Rue Blaise Pascal, F-67070 Strasbourg, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 12期

关键词：

ARYL HALIDES; HETEROGENEOUS CATALYST; COPPER NANOPARTICLES; COUPLING REACTIONS; HIGHLY EFFICIENT; CLICK CHEMISTRY; GREEN CATALYSTS; BOND FORMATION; ORGANIC-SYNTHESIS; ZEOLITES;

D O I：

10.1021/acs.joc.8b00620

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper(I)-doped zeolite Cu-I-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.

引用

页码：6408 / 6422

页数：15

共 96 条

[1] BIS(CYCLOPENTADIENYLIRON)ARENE COMPLEXES - A NEW ROUTE TO THE SYNTHESIS AND FUNCTIONALIZATION OF POLYAROMATIC ETHERS [J].