A Redox-Switchable Gold(I) Complex for the Hydroamination of Acetylenes: A Convenient Way for Studying Ligand-Derived Electronic Effects

被引：19

作者：

Ruiz-Zambrana, Cesar ^{[1
]}

Poyatos, Macarena ^{[1
]}

Peris, Eduardo ^{[1
]}

机构：

[1] Univ Jaume I RINGGOLD, Ctr Innovac Quim Avanzada ORFEO CINQA, Inst Adv Mat INAM, E-12071 Castellon de La Plana, Spain

来源：

ACS CATALYSIS | 2022年 / 12卷 / 08期

关键词：

redox-switchable; hydroamination of alkynes; gold; mechanism; N-heterocyclic carbene; homogeneous catalysis; ACTIVE MESOIONIC CARBENES; N-HETEROCYCLIC CARBENE; NON-INNOCENT LIGANDS; INTERMOLECULAR HYDROAMINATION; CATALYSIS; REACTIVITY; ALKYNES; DESIGN;

D O I：

10.1021/acscatal.2c00613

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A gold complex with a naphthalene-di-imide-functionalized N-heterocyclic carbene (NHC) ligand was preparedand characterized. The electrochemical studies reveal that thecomplex is able to undergo two successive reduction events,associated to the reduction of the NDI moiety of the NHC ligand.Once the redox-switchable properties of this Au(I) complex wereproven, the complex was tested in the hydroamination of terminalalkynes. The activity of the neutral complex was moderate-to-highfor this reaction, but the one-electron reduced species did notshow any activity in the reaction. The activity of the catalyst couldbe toggled offand on several times by successively adding areducing agent (cobaltocene) or an oxidant (acetylferroceniumtetrafluoroborate). The results indicate that the rate-determining step of the catalytic cycle is the nucleophilic attack of the amine on the Au-coordinated alkyne

引用

页码：4465 / 4472

页数：8

共 54 条

[1] Reversible C-F bond formation and the Au-catalyzed hydrofluorination of alkynes [J].