Perfluoro-tagged, phosphine-free palladium nanoparticles supported on silica gel: application to alkynylation of aryl halides, Suzuki-Miyaura cross-coupling, and Heck reactions under aerobic conditions

被引：99

作者：

Bernini, Roberta ^{[1
,2
]}

Cacchi, Sandro ^{[3
]}

Fabrizi, Giancarlo ^{[3
]}

Forte, Giovanni ^{[4
]}

Petrucci, Francesco ^{[4
]}

Prastaro, Alessandro ^{[1
,2
]}

Niembro, Sandra ^{[5
]}

Shafir, Alexandr ^{[5
]}

Vallribera, Adelina ^{[5
]}

机构：

[1] Univ Tuscia, Dipartimento ABAC, I-01100 Viterbo, Italy

[2] Consorzio Univ La Chim per lAmbiente, I-01100 Viterbo, Italy

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

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

[5] Univ Autonoma Barcelona, Dept Chem, Cerdanyola Del Valles 08193, Spain

来源：

GREEN CHEMISTRY | 2010年 / 12卷 / 01期

关键词：

CARBON AEROGELS; CATALYZED REACTIONS; ROOM-TEMPERATURE; TERMINAL ALKYNES; PD NANOPARTICLES; 1,4-DISUBSTITUTED 1,3-DIYNES; POLYUREA MICROCAPSULES; SONOGASHIRA REACTIONS; METAL NANOPARTICLES; REUSABLE CATALYST;

D O I：

10.1039/b915465e

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

The utilization of perfluoro-tagged palladium nanoparticles immobilized on fluorous silica gel through fluorous-fluorous interactions (Pd-np-A/FSG) or through covalent bonding to silica gel (Pd-np-B) in the alkynylation of aryl halides, in the Suzuki-Miyaura cross-coupling, as well as in the Heck reaction between methyl acrylate and aryl iodides is described. The reactions are carried out under aerobic and phosphine-free conditions with excellent to quantitative product yields in each case. The catalysts are easily recovered and reused several times without significant loss of activity. The alkynylation of aryl halides (under copper-free conditions) and the Suzuki-Miyaura cross-coupling are carried out in water. The Heck reaction of methyl acrylate with aryl iodides is best performed in MeCN. The utilization of Pd-np-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl) trifluoroacetanilides and aryl halides is also reported.

引用

页码：150 / 158

页数：9

共 81 条

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