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

Roberta Bernini; Sandro Cacchi; Giancarlo Fabrizi; Giovanni Forte; Francesco Petrucci; Alessandro Prastaro; Sandra Niembro; Alexandr Shafir; Adelina Vallribera

doi:10.1039/b915465e

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

Roberta Bernini, Sandro Cacchi, Giancarlo Fabrizi, Giovanni Forte, Francesco Petrucci, Alessandro Prastaro, Sandra Niembro, Alexandr Shafir, Adelina Vallribera

Department of Chemistry

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

107 Citations (Scopus)

Abstract

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 Pdnp-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl)trifluoroacetanilides and aryl halides is also reported. © 2010 The Royal Society of Chemistry.

Original language	English
Pages (from-to)	150-158
Journal	Green Chemistry
Volume	12
Issue number	1
DOIs	https://doi.org/10.1039/b915465e
Publication status	Published - 26 Feb 2010

Access to Document

10.1039/b915465e

Cite this

Bernini, R., Cacchi, S., Fabrizi, G., Forte, G., Petrucci, F., Prastaro, A., Niembro, S., Shafir, A., & Vallribera, A. (2010). 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. Green Chemistry, 12(1), 150-158. https://doi.org/10.1039/b915465e

@article{481c1b6daae94bbcab37077c38f4ea82,

title = "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",

abstract = "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 Pdnp-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl)trifluoroacetanilides and aryl halides is also reported. {\textcopyright} 2010 The Royal Society of Chemistry.",

author = "Roberta Bernini and Sandro Cacchi and Giancarlo Fabrizi and Giovanni Forte and Francesco Petrucci and Alessandro Prastaro and Sandra Niembro and Alexandr Shafir and Adelina Vallribera",

year = "2010",

month = feb,

day = "26",

doi = "10.1039/b915465e",

language = "English",

volume = "12",

pages = "150--158",

journal = "Green Chemistry",

issn = "1463-9262",

number = "1",

}

Bernini, R, Cacchi, S, Fabrizi, G, Forte, G, Petrucci, F, Prastaro, A, Niembro, S, Shafir, A & Vallribera, A 2010, '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', Green Chemistry, vol. 12, no. 1, pp. 150-158. https://doi.org/10.1039/b915465e

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. / Bernini, Roberta; Cacchi, Sandro; Fabrizi, Giancarlo et al.

In: Green Chemistry, Vol. 12, No. 1, 26.02.2010, p. 150-158.

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

TY - JOUR

T1 - 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

AU - Bernini, Roberta

AU - Cacchi, Sandro

AU - Fabrizi, Giancarlo

AU - Forte, Giovanni

AU - Petrucci, Francesco

AU - Prastaro, Alessandro

AU - Niembro, Sandra

AU - Shafir, Alexandr

AU - Vallribera, Adelina

PY - 2010/2/26

Y1 - 2010/2/26

N2 - 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 Pdnp-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl)trifluoroacetanilides and aryl halides is also reported. © 2010 The Royal Society of Chemistry.

AB - 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 Pdnp-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl)trifluoroacetanilides and aryl halides is also reported. © 2010 The Royal Society of Chemistry.

U2 - 10.1039/b915465e

DO - 10.1039/b915465e

M3 - Article

SN - 1463-9262

VL - 12

SP - 150

EP - 158

JO - Green Chemistry

JF - Green Chemistry

IS - 1

ER -

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

Abstract

Access to Document

Fingerprint

Cite this