Heck, Sonogashira, and Hiyama reactions catalyzed by palladium nanoparticles stabilized by tris-imidazolium salt

Marc Planellas; Yanina Moglie; Francisco Alonso; Miguel Yus; Roser Pleixats; Alexandr Shafir

doi:10.1002/ejoc.201400162

Heck, Sonogashira, and Hiyama reactions catalyzed by palladium nanoparticles stabilized by tris-imidazolium salt

Marc Planellas, Yanina Moglie, Francisco Alonso, Miguel Yus, Roser Pleixats, Alexandr Shafir

Department of Chemistry

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

26 Citations (Scopus)

Abstract

Palladium nanoparticles, prepared by the hydrogenation of Pd(dba) 2 in the presence of a tris-imidazolium iodide as stabilizer, act as an efficient catalyst for Heck and copper-free Sonogashira reactions with a range of aryl iodides and bromides at 0.2 mol-% Pd loading. Moreover, we describe a convenient protocol for the fluoride-free Hiyama coupling of vinylsilanes with aryl iodides that involves the use of sodium hydroxide as promoter in a methanol/water mixture. Under the developed conditions, one-pot, double Heck and Hiyama-Heck reactions are successfully achieved. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	3001-3008
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	14
DOIs	https://doi.org/10.1002/ejoc.201400162
Publication status	Published - 1 Jan 2014

Keywords

Cross-coupling
Heterogeneous catalysis
Nanoparticles
Palladium

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title = "Heck, Sonogashira, and Hiyama reactions catalyzed by palladium nanoparticles stabilized by tris-imidazolium salt",

abstract = "Palladium nanoparticles, prepared by the hydrogenation of Pd(dba) 2 in the presence of a tris-imidazolium iodide as stabilizer, act as an efficient catalyst for Heck and copper-free Sonogashira reactions with a range of aryl iodides and bromides at 0.2 mol-% Pd loading. Moreover, we describe a convenient protocol for the fluoride-free Hiyama coupling of vinylsilanes with aryl iodides that involves the use of sodium hydroxide as promoter in a methanol/water mixture. Under the developed conditions, one-pot, double Heck and Hiyama-Heck reactions are successfully achieved. {\textcopyright} 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "Cross-coupling, Heterogeneous catalysis, Nanoparticles, Palladium",

author = "Marc Planellas and Yanina Moglie and Francisco Alonso and Miguel Yus and Roser Pleixats and Alexandr Shafir",

year = "2014",

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doi = "10.1002/ejoc.201400162",

language = "English",

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Heck, Sonogashira, and Hiyama reactions catalyzed by palladium nanoparticles stabilized by tris-imidazolium salt. / Planellas, Marc; Moglie, Yanina; Alonso, Francisco; Yus, Miguel; Pleixats, Roser ; Shafir, Alexandr.

In: European Journal of Organic Chemistry, Vol. 2014, No. 14, 01.01.2014, p. 3001-3008.

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

TY - JOUR

T1 - Heck, Sonogashira, and Hiyama reactions catalyzed by palladium nanoparticles stabilized by tris-imidazolium salt

AU - Planellas, Marc

AU - Moglie, Yanina

AU - Alonso, Francisco

AU - Yus, Miguel

AU - Pleixats, Roser

AU - Shafir, Alexandr

PY - 2014/1/1

Y1 - 2014/1/1

N2 - Palladium nanoparticles, prepared by the hydrogenation of Pd(dba) 2 in the presence of a tris-imidazolium iodide as stabilizer, act as an efficient catalyst for Heck and copper-free Sonogashira reactions with a range of aryl iodides and bromides at 0.2 mol-% Pd loading. Moreover, we describe a convenient protocol for the fluoride-free Hiyama coupling of vinylsilanes with aryl iodides that involves the use of sodium hydroxide as promoter in a methanol/water mixture. Under the developed conditions, one-pot, double Heck and Hiyama-Heck reactions are successfully achieved. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - Palladium nanoparticles, prepared by the hydrogenation of Pd(dba) 2 in the presence of a tris-imidazolium iodide as stabilizer, act as an efficient catalyst for Heck and copper-free Sonogashira reactions with a range of aryl iodides and bromides at 0.2 mol-% Pd loading. Moreover, we describe a convenient protocol for the fluoride-free Hiyama coupling of vinylsilanes with aryl iodides that involves the use of sodium hydroxide as promoter in a methanol/water mixture. Under the developed conditions, one-pot, double Heck and Hiyama-Heck reactions are successfully achieved. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - Cross-coupling

KW - Heterogeneous catalysis

KW - Nanoparticles

KW - Palladium

U2 - 10.1002/ejoc.201400162

DO - 10.1002/ejoc.201400162

M3 - Article

VL - 2014

SP - 3001

EP - 3008

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