Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species?

Christoph G. Baumann; Sara De Ornellas; Jonathan P. Reeds; Thomas E. Storr; Thomas J. Williams; Ian J S Fairlamb

doi:10.1016/j.tet.2014.06.002

Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species?

Christoph G. Baumann, Sara De Ornellas, Jonathan P. Reeds, Thomas E. Storr, Thomas J. Williams, Ian J S Fairlamb^*

^*Corresponding author for this work

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

Abstract

Abstract Examination of a series of C-H bond functionalization reactions of heteroarenes (e.g., indole, benzoxazole, benzthiazole, benzimidazole and purine derivatives) mediated by Pd(OAc)₂, a commonly used C-H bond functionalization catalyst, reveals that well-defined Pd nanoparticles (PdNPs) are rapidly formed under working catalyst conditions. The PdNPs can be characterized ex situ after entrapment in a polymer matrix (polyvinylpyrrolidinone, PVP). Independently synthesized Pd(PVP)NPs are catalytically competent species, exhibiting catalyst activity commensurate with Pd(OAc)₂ in several C-H bond functionalization reactions. Across a range of reactions, Pd concentration is a common variable, which can be linked to the propagation of PdNPs under working catalytic conditions using polar solvents like DMF, DMSO and acetic acid.

Original language	English
Article number	25667
Pages (from-to)	6174-6187
Number of pages	14
Journal	Tetrahedron
Volume	70
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2014.06.002
Publication status	Published - 29 May 2015

Keywords

Catalysis
Cross-coupling
Nanoparticles
Palladium

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Baumann, C. G., De Ornellas, S., Reeds, J. P., Storr, T. E., Williams, T. J., & Fairlamb, I. J. S. (2015). Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species? Tetrahedron, 70(36), 6174-6187. Article 25667. https://doi.org/10.1016/j.tet.2014.06.002

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title = "Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species?",

abstract = "Abstract Examination of a series of C-H bond functionalization reactions of heteroarenes (e.g., indole, benzoxazole, benzthiazole, benzimidazole and purine derivatives) mediated by Pd(OAc)2, a commonly used C-H bond functionalization catalyst, reveals that well-defined Pd nanoparticles (PdNPs) are rapidly formed under working catalyst conditions. The PdNPs can be characterized ex situ after entrapment in a polymer matrix (polyvinylpyrrolidinone, PVP). Independently synthesized Pd(PVP)NPs are catalytically competent species, exhibiting catalyst activity commensurate with Pd(OAc)2 in several C-H bond functionalization reactions. Across a range of reactions, Pd concentration is a common variable, which can be linked to the propagation of PdNPs under working catalytic conditions using polar solvents like DMF, DMSO and acetic acid.",

keywords = "Catalysis, Cross-coupling, Nanoparticles, Palladium",

author = "Baumann, {Christoph G.} and {De Ornellas}, Sara and Reeds, {Jonathan P.} and Storr, {Thomas E.} and Williams, {Thomas J.} and Fairlamb, {Ian J S}",

year = "2015",

month = may,

day = "29",

doi = "10.1016/j.tet.2014.06.002",

language = "English",

volume = "70",

pages = "6174--6187",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "36",

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Baumann, CG, De Ornellas, S, Reeds, JP, Storr, TE, Williams, TJ & Fairlamb, IJS 2015, 'Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species?', Tetrahedron, vol. 70, no. 36, 25667, pp. 6174-6187. https://doi.org/10.1016/j.tet.2014.06.002

Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species? / Baumann, Christoph G.; De Ornellas, Sara; Reeds, Jonathan P. et al.
In: Tetrahedron, Vol. 70, No. 36, 25667, 29.05.2015, p. 6174-6187.

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

TY - JOUR

T1 - Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes

T2 - Are nanoparticles a moribund form of Pd or an active catalytic species?

AU - Baumann, Christoph G.

AU - De Ornellas, Sara

AU - Reeds, Jonathan P.

AU - Storr, Thomas E.

AU - Williams, Thomas J.

AU - Fairlamb, Ian J S

PY - 2015/5/29

Y1 - 2015/5/29

N2 - Abstract Examination of a series of C-H bond functionalization reactions of heteroarenes (e.g., indole, benzoxazole, benzthiazole, benzimidazole and purine derivatives) mediated by Pd(OAc)2, a commonly used C-H bond functionalization catalyst, reveals that well-defined Pd nanoparticles (PdNPs) are rapidly formed under working catalyst conditions. The PdNPs can be characterized ex situ after entrapment in a polymer matrix (polyvinylpyrrolidinone, PVP). Independently synthesized Pd(PVP)NPs are catalytically competent species, exhibiting catalyst activity commensurate with Pd(OAc)2 in several C-H bond functionalization reactions. Across a range of reactions, Pd concentration is a common variable, which can be linked to the propagation of PdNPs under working catalytic conditions using polar solvents like DMF, DMSO and acetic acid.

AB - Abstract Examination of a series of C-H bond functionalization reactions of heteroarenes (e.g., indole, benzoxazole, benzthiazole, benzimidazole and purine derivatives) mediated by Pd(OAc)2, a commonly used C-H bond functionalization catalyst, reveals that well-defined Pd nanoparticles (PdNPs) are rapidly formed under working catalyst conditions. The PdNPs can be characterized ex situ after entrapment in a polymer matrix (polyvinylpyrrolidinone, PVP). Independently synthesized Pd(PVP)NPs are catalytically competent species, exhibiting catalyst activity commensurate with Pd(OAc)2 in several C-H bond functionalization reactions. Across a range of reactions, Pd concentration is a common variable, which can be linked to the propagation of PdNPs under working catalytic conditions using polar solvents like DMF, DMSO and acetic acid.

KW - Catalysis

KW - Cross-coupling

KW - Nanoparticles

KW - Palladium

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U2 - 10.1016/j.tet.2014.06.002

DO - 10.1016/j.tet.2014.06.002

M3 - Article

AN - SCOPUS:84925880906

SN - 0040-4020

VL - 70

SP - 6174

EP - 6187

JO - Tetrahedron

JF - Tetrahedron

IS - 36

M1 - 25667

ER -

Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species?

Abstract

Keywords

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