Recyclable Polyethylene Glycol Ubiquinol Succinate-Bound N-Heterocyclic Carbene-Gold(I) Complexes: Sustainable Micellar Catalysis in Water

被引：8

作者：

Ballmann, Monika ^{[1
]}

Ruer, Paul C. ^{[1
]}

Hofnagel, Oliver ^{[2
]}

Hiller, Wolf ^{[1
]}

Krause, Norbert ^{[1
]}

机构：

[1] TU Dortmund Univ, Organ Chem, D-44227 Dortmund, Germany

[2] Max Planck Inst Mol Physiol, Dept Struct Biochem, D-44227 Dortmund, Germany

来源：

ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2022年 / 10卷 / 22期

关键词：

Gold catalysis; Micellar catalysis; Water-soluble catalysts; Catalyst recycling; Dehydrative cyclization; Cosurfactants; Water; Cyclizations; Green chemistry; ROOM-TEMPERATURE; SURFACTANTS; POLYANILINE; LIGAND; PQS;

D O I：

10.1021/acssuschemeng.2c00713

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient synthesis of three amphiphilic polyethylene glycol ubiquinol succinate (PQS)-bound N-heterocyclic carbene (NHC)-gold(I) complexes as micellar catalysts in bulk water was developed. The surfactant-bound gold catalysts were applied in three different cyclization reactions of acetylenic or allenic substrates, with the main focus being the gold-catalyzed dehydrative cyclization of alkynediols to furans. An effective recycling of the designer surfactant-bound NHC-gold(I) catalysts in water was demonstrated for all cyclization reactions. With sodium dodecyl sulfate as the cosurfactant, a significant acceleration of the catalytic reactions was observed. Mechanistic investigations of the gold-catalyzed dehydrative cyclization of alkynediols point to possible causes for this acceleration effect.

引用

页码：7288 / 7298

页数：11

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