The Heck Reaction of Allylic Alcohols Catalyzed by Palladium Nanoparticles in Water: Chemoenzymatic Synthesis of (R)-(-)-Rhododendrol

被引：68

作者：

Boffi, Alberto ^{[2
]}

Cacchi, Sandro ^{[1
]}

Ceci, Pierpaolo ^{[3
]}

Cirilli, Roberto ^{[4
]}

Fabrizi, Giancarlo ^{[1
]}

Prastaro, Alessandro ^{[1
]}

Niembro, Sandra ^{[5
]}

Shafir, Alexandr ^{[5
]}

Vallribera, Adelina ^{[5
]}

机构：

[1] Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy

[2] Univ Rome, Dipartimento Sci Biochim, I-00185 Rome, Italy

[3] CNR, Ist Biol & Patol Mol, I-00185 Rome, Italy

[4] Ist Super Sanita, Dipartimento Farmaco, I-00161 Rome, Italy

[5] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain

来源：

CHEMCATCHEM | 2011年 / 3卷 / 02期

关键词：

enzyme catalysis; nanoparticles; one-pot reactions; palladium; water; CROSS-COUPLING REACTIONS; HIGHLY SELECTIVE SYNTHESIS; ONE-POT SYNTHESES; ARYL HALIDES; ARYLBORONIC ACIDS; AQUEOUS-MEDIA; BORONIC ACIDS; SUBSTITUTION-REACTIONS; PHOSPHINE COMPLEXES; ORGANIC HALIDES;

D O I：

10.1002/cctc.201000260

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：

The use of phosphine-free perfluoro-tagged palladium nanoparticles immobilized on fluorous silica gel (FSG), either through fluorous-fluorous interactions or covalent bonding, in the Heck reaction of aryl iodides with allylic alcohols under aerobic conditions in water is described. 4-(4-Methoxyphenyl)butan-2-one, an important fine chemical, is readily accessed by this procedure. A two-step one-pot process, involving a Heck reaction followed by an enantioselective enzyme-catalyzed reduction, to form chiral alcohols is applied to the synthesis of (R)-(-)-rhododendrol. The palladium catalysts can be recycled several times, both in the Heck reaction and in the one-pot chemoenzymatic process.

引用

页码：347 / 353

页数：7

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