Dendrimer-encapsulated Pd nanoparticles as catalysts for C-C cross-couplings in flow microreactors

被引：22

作者：

Ricciardi, Roberto ^{[1
]}

Huskens, Jurriaan ^{[1
]}

Verboom, Willem ^{[1
]}

机构：

[1] Univ Twente, MESA Inst Nanotechnol, Lab Mol Nanofabricat, NL-7500 AE Enschede, Netherlands

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 17期

关键词：

PALLADIUM NANOPARTICLES; ACETYLENE DERIVATIVES; OXIDATIVE ADDITION; ORGANIC-SYNTHESIS; SUZUKI REACTION; SONOGASHIRA; METAL; ARYL; EFFICIENT; HECK;

D O I：

10.1039/c5ob00289c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The inner walls of glass microreactors were functionalized with dendrimer-encapsulated Pd nanoparticles. The catalysts were efficient for the Heck-Cassar (copper-free Sonogashira) and Suzuki-Miyaura (SMC) cross-coupling reactions. For the Heck-Cassar reaction between iodobenzene and phenylacetylene, the catalytic system exhibited a high turnover frequency (TOF) and on average required milder reaction conditions as compared to other continuous flow cross-couplings. A study of the substituent effect of para-substituted aryl halides revealed a beneficial effect of electron-withdrawing side groups for the SMC. Moreover, a reaction constant (rho) of 1.5, determined from the Hammett plot, indicated a possible rate-determining step other than the oxidative addition.

引用

页码：4953 / 4959

页数：7

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