1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuC≡CPh): An inorganic version of a click reaction

Trevor J. Del Castillo; Soumya Sarkar; Khalil A. Abboud; Adam S. Veige

doi:10.1039/c1dt10787a

1,3-Dipolar cycloaddition between a metal–azide (Ph₃PAuN₃) and a metal–acetylide (Ph₃PAuC≡CPh): An inorganic version of a click reaction

Trevor J. Del Castillo, Soumya Sarkar, Khalil A. Abboud, Adam S. Veige

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

77 Scopus citations

Abstract

This report describes the synthesis and characterization of 1,5-bis-triphenylphosphinegold(i) 1,2,3-triazolate (3 _(1,5)). The synthesis of the dinuclear complex 3 _(1,5) is achieved via an unprecedented inorganic click (iClick) reaction between the metal–azide PPh₃AuN₃ (1) and the metal–acetylide PPh₃Au–C≡CPh (2). Characterization of 3 _(1,5) includes multinuclear NMR spectroscopy, combustion analysis, and single crystal X-ray crystallography. Experimental characterization is complemented with density-functional-theory (DFT) calculations which indicate the 1,4-isomer 3 _(1,4) is less stable by 3.3 kcal mol⁻¹. The energetic difference lies primarily in the ability of the phenyl group in the 4-position of 3 _(1,5) to lie coplanar with the triazolate to create a delocalized Π-bonding HOMO orbital.

Original language	English (US)
Pages (from-to)	8140-8144
Number of pages	5
Journal	Journal of the Chemical Society. Dalton Transactions
Volume	40
Issue number	32
DOIs	https://doi.org/10.1039/c1dt10787a
State	Published - Aug 2 2011
Externally published	Yes

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General Chemistry

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title = "1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuC≡CPh): An inorganic version of a click reaction",

abstract = "This report describes the synthesis and characterization of 1,5-bis-triphenylphosphinegold(i) 1,2,3-triazolate (3 (1,5)). The synthesis of the dinuclear complex 3 (1,5) is achieved via an unprecedented inorganic click (iClick) reaction between the metal–azide PPh3AuN3 (1) and the metal–acetylide PPh3Au–C≡CPh (2). Characterization of 3 (1,5) includes multinuclear NMR spectroscopy, combustion analysis, and single crystal X-ray crystallography. Experimental characterization is complemented with density-functional-theory (DFT) calculations which indicate the 1,4-isomer 3 (1,4) is less stable by 3.3 kcal mol−1. The energetic difference lies primarily in the ability of the phenyl group in the 4-position of 3 (1,5) to lie coplanar with the triazolate to create a delocalized Π-bonding HOMO orbital.",

author = "{Del Castillo}, {Trevor J.} and Soumya Sarkar and Abboud, {Khalil A.} and Veige, {Adam S.}",

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journal = "Journal of the Chemical Society. Dalton Transactions",

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publisher = "Royal Society of Chemistry",

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1,3-Dipolar cycloaddition between a metal–azide (Ph₃PAuN₃) and a metal–acetylide (Ph₃PAuC≡CPh): An inorganic version of a click reaction. / Del Castillo, Trevor J.; Sarkar, Soumya; Abboud, Khalil A. et al.
In: Journal of the Chemical Society. Dalton Transactions, Vol. 40, No. 32, 02.08.2011, p. 8140-8144.

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

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T1 - 1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuC≡CPh)

T2 - An inorganic version of a click reaction

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AU - Abboud, Khalil A.

AU - Veige, Adam S.

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N2 - This report describes the synthesis and characterization of 1,5-bis-triphenylphosphinegold(i) 1,2,3-triazolate (3 (1,5)). The synthesis of the dinuclear complex 3 (1,5) is achieved via an unprecedented inorganic click (iClick) reaction between the metal–azide PPh3AuN3 (1) and the metal–acetylide PPh3Au–C≡CPh (2). Characterization of 3 (1,5) includes multinuclear NMR spectroscopy, combustion analysis, and single crystal X-ray crystallography. Experimental characterization is complemented with density-functional-theory (DFT) calculations which indicate the 1,4-isomer 3 (1,4) is less stable by 3.3 kcal mol−1. The energetic difference lies primarily in the ability of the phenyl group in the 4-position of 3 (1,5) to lie coplanar with the triazolate to create a delocalized Π-bonding HOMO orbital.

AB - This report describes the synthesis and characterization of 1,5-bis-triphenylphosphinegold(i) 1,2,3-triazolate (3 (1,5)). The synthesis of the dinuclear complex 3 (1,5) is achieved via an unprecedented inorganic click (iClick) reaction between the metal–azide PPh3AuN3 (1) and the metal–acetylide PPh3Au–C≡CPh (2). Characterization of 3 (1,5) includes multinuclear NMR spectroscopy, combustion analysis, and single crystal X-ray crystallography. Experimental characterization is complemented with density-functional-theory (DFT) calculations which indicate the 1,4-isomer 3 (1,4) is less stable by 3.3 kcal mol−1. The energetic difference lies primarily in the ability of the phenyl group in the 4-position of 3 (1,5) to lie coplanar with the triazolate to create a delocalized Π-bonding HOMO orbital.

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1,3-Dipolar cycloaddition between a metal–azide (Ph₃PAuN₃) and a metal–acetylide (Ph₃PAuC≡CPh): An inorganic version of a click reaction

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