Recyclable hybrid silica-based catalysts derived from Pd-NHC complexes for suzuki, heck and sonogashira reactions

Guadalupe Borja; Amàlia Monge-Marcet; Roser Pleixats; Teodor Parella; Xavier Cattoën; Michel Wong Chi Man

doi:10.1002/ejoc.201200205

Recyclable hybrid silica-based catalysts derived from Pd-NHC complexes for suzuki, heck and sonogashira reactions

Guadalupe Borja, Amàlia Monge-Marcet, Roser Pleixats, Teodor Parella, Xavier Cattoën, Michel Wong Chi Man

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

75 Citations (Scopus)

Abstract

Two silylated Pd-NHC complexes were immobilized on hybrid silicas by sol-gel cocondensation with tetraethyl orthosilicate (TEOS) and performed well as recyclable catalysts towards the Heck, Suzuki, and Sonogashira coupling reactions. Remarkable conversion and recyclability were achieved in the Suzuki reaction with a challenging aryl chloride. No side products and no undesired homocoupling were observed in Suzuki or Heck reactions, which facilitates the final purification step for the cross-coupling products. High turnover numbers and turnover frequencies were found for copper- and phosphane-free Sonogashira reaction between p-bromoacetophenone and phenylacetylene. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	3625-3635
Journal	European Journal of Organic Chemistry
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.201200205
Publication status	Published - 1 Jul 2012

Keywords

C-C coupling
Carbenes
Cross-coupling
Green chemistry
Heterogeneous catalysis
Palladium
Sol-gel processes
Supported catalysts

Access to Document

10.1002/ejoc.201200205

Cite this

@article{f43f6d33c6ef48408ed50b5ac8f57cdc,

title = "Recyclable hybrid silica-based catalysts derived from Pd-NHC complexes for suzuki, heck and sonogashira reactions",

abstract = "Two silylated Pd-NHC complexes were immobilized on hybrid silicas by sol-gel cocondensation with tetraethyl orthosilicate (TEOS) and performed well as recyclable catalysts towards the Heck, Suzuki, and Sonogashira coupling reactions. Remarkable conversion and recyclability were achieved in the Suzuki reaction with a challenging aryl chloride. No side products and no undesired homocoupling were observed in Suzuki or Heck reactions, which facilitates the final purification step for the cross-coupling products. High turnover numbers and turnover frequencies were found for copper- and phosphane-free Sonogashira reaction between p-bromoacetophenone and phenylacetylene. {\textcopyright} 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "C-C coupling, Carbenes, Cross-coupling, Green chemistry, Heterogeneous catalysis, Palladium, Sol-gel processes, Supported catalysts",

author = "Guadalupe Borja and Am{\`a}lia Monge-Marcet and Roser Pleixats and Teodor Parella and Xavier Catto{\"e}n and {Wong Chi Man}, Michel",

year = "2012",

month = jul,

day = "1",

doi = "10.1002/ejoc.201200205",

language = "English",

pages = "3625--3635",

number = "19",

}

TY - JOUR

T1 - Recyclable hybrid silica-based catalysts derived from Pd-NHC complexes for suzuki, heck and sonogashira reactions

AU - Borja, Guadalupe

AU - Monge-Marcet, Amàlia

AU - Pleixats, Roser

AU - Parella, Teodor

AU - Cattoën, Xavier

AU - Wong Chi Man, Michel

PY - 2012/7/1

Y1 - 2012/7/1

N2 - Two silylated Pd-NHC complexes were immobilized on hybrid silicas by sol-gel cocondensation with tetraethyl orthosilicate (TEOS) and performed well as recyclable catalysts towards the Heck, Suzuki, and Sonogashira coupling reactions. Remarkable conversion and recyclability were achieved in the Suzuki reaction with a challenging aryl chloride. No side products and no undesired homocoupling were observed in Suzuki or Heck reactions, which facilitates the final purification step for the cross-coupling products. High turnover numbers and turnover frequencies were found for copper- and phosphane-free Sonogashira reaction between p-bromoacetophenone and phenylacetylene. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - Two silylated Pd-NHC complexes were immobilized on hybrid silicas by sol-gel cocondensation with tetraethyl orthosilicate (TEOS) and performed well as recyclable catalysts towards the Heck, Suzuki, and Sonogashira coupling reactions. Remarkable conversion and recyclability were achieved in the Suzuki reaction with a challenging aryl chloride. No side products and no undesired homocoupling were observed in Suzuki or Heck reactions, which facilitates the final purification step for the cross-coupling products. High turnover numbers and turnover frequencies were found for copper- and phosphane-free Sonogashira reaction between p-bromoacetophenone and phenylacetylene. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - C-C coupling

KW - Carbenes

KW - Cross-coupling

KW - Green chemistry

KW - Heterogeneous catalysis

KW - Palladium

KW - Sol-gel processes

KW - Supported catalysts

U2 - 10.1002/ejoc.201200205

DO - 10.1002/ejoc.201200205

M3 - Article

SP - 3625

EP - 3635

IS - 19

ER -

Recyclable hybrid silica-based catalysts derived from Pd-NHC complexes for suzuki, heck and sonogashira reactions

Abstract

Keywords

Access to Document

Fingerprint

Cite this