Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling: Activity of the palladium complex in Suzuki-Miyaura cross-coupling

Emma K. Bullough; Marc A. Little; Charlotte E. Willans

doi:10.1021/om301085s

Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling: Activity of the palladium complex in Suzuki-Miyaura cross-coupling

Emma K. Bullough, Marc A. Little, Charlotte E. Willans^*

^*Corresponding author for this work

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

46 Citations (Scopus)

Abstract

A novel N-heterocyclic carbene 1,3-alternate calix[4]arene complex bearing four palladium(II) centers per ligand has been prepared. Electrochemical synthetic methods were used to prepare the corresponding copper(I) complex, followed by transmetalation onto palladium(II). The activity of the palladium complex was probed in the Suzuki-Miyaura cross-coupling reaction. An inverse correlation between palladium concentration and activity was observed, with the results indicating that calix[4]arenes in the cone conformation may reduce the aggregation of palladium(0) nanoclusters, whereas our 1,3-alternate calix[4]arene does not provide any supramolecular stabilizing effect.

Original language	English
Pages (from-to)	570-577
Number of pages	8
Journal	Organometallics
Volume	32
Issue number	2
DOIs	https://doi.org/10.1021/om301085s
Publication status	Published - 28 Jan 2013

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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Bullough, E. K., Little, M. A., & Willans, C. E. (2013). Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling: Activity of the palladium complex in Suzuki-Miyaura cross-coupling. Organometallics, 32(2), 570-577. https://doi.org/10.1021/om301085s

Bullough, Emma K. ; Little, Marc A. ; Willans, Charlotte E. / Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling : Activity of the palladium complex in Suzuki-Miyaura cross-coupling. In: Organometallics. 2013 ; Vol. 32, No. 2. pp. 570-577.

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title = "Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling: Activity of the palladium complex in Suzuki-Miyaura cross-coupling",

abstract = "A novel N-heterocyclic carbene 1,3-alternate calix[4]arene complex bearing four palladium(II) centers per ligand has been prepared. Electrochemical synthetic methods were used to prepare the corresponding copper(I) complex, followed by transmetalation onto palladium(II). The activity of the palladium complex was probed in the Suzuki-Miyaura cross-coupling reaction. An inverse correlation between palladium concentration and activity was observed, with the results indicating that calix[4]arenes in the cone conformation may reduce the aggregation of palladium(0) nanoclusters, whereas our 1,3-alternate calix[4]arene does not provide any supramolecular stabilizing effect.",

author = "Bullough, {Emma K.} and Little, {Marc A.} and Willans, {Charlotte E.}",

year = "2013",

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doi = "10.1021/om301085s",

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Bullough, EK, Little, MA & Willans, CE 2013, 'Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling: Activity of the palladium complex in Suzuki-Miyaura cross-coupling', Organometallics, vol. 32, no. 2, pp. 570-577. https://doi.org/10.1021/om301085s

Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling: Activity of the palladium complex in Suzuki-Miyaura cross-coupling. / Bullough, Emma K.; Little, Marc A.; Willans, Charlotte E.
In: Organometallics, Vol. 32, No. 2, 28.01.2013, p. 570-577.

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

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T1 - Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling

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AB - A novel N-heterocyclic carbene 1,3-alternate calix[4]arene complex bearing four palladium(II) centers per ligand has been prepared. Electrochemical synthetic methods were used to prepare the corresponding copper(I) complex, followed by transmetalation onto palladium(II). The activity of the palladium complex was probed in the Suzuki-Miyaura cross-coupling reaction. An inverse correlation between palladium concentration and activity was observed, with the results indicating that calix[4]arenes in the cone conformation may reduce the aggregation of palladium(0) nanoclusters, whereas our 1,3-alternate calix[4]arene does not provide any supramolecular stabilizing effect.

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Electrochemical Synthesis of a Tetradentate Copper N-Heterocyclic Carbene Calix[4]Arene and Its Transmetalation to Palladium: Activity of the Palladium Complex in Suzuki-Miyaura Cross-Coupling: Activity of the palladium complex in Suzuki-Miyaura cross-coupling

Abstract

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