4-Hydroxyaryl complexes of group 10 metals

Shiu Chun So; Wai Man Cheung; Herman H.Y. Sung; Ian D. Williams; Wa Hung Leung

doi:10.1016/j.jorganchem.2017.10.012

4-Hydroxyaryl complexes of group 10 metals

Shiu Chun So
, Wai Man Cheung
, Herman H.Y. Sung
, Ian D. Williams
, Wa Hung Leung^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Short survey › peer-review

3 Citations (Scopus)

Abstract

Attempts have been made to synthesize group 10 metal complexes bearing σ-bonded 4-hydroxyaryl ligands that are potential precursors to metallaquinones. Treatment of 4-bromo-2,6-di-tert-butylphenol with [Pd(PPh₃)₄] led to formation of the phosphaquinone Ph₃P = C₆H₃^tBu₂-3,5-O-4 (1), whereas that with [M(PPh₃)₄] (M = Ni, Pt) yielded the biquinone [C₆H₃^tBu₂-3,5-O-4]₂ (2). The solid-state structure of 1 features a short C=O double bond and alternate phenyl C-C single and double bonds that are characteristic of quinoidal compounds. Alkylation of [NiCl₂(PPh₃)₂] with (C₆H₂Me₂-3,5-OSiMe₃-4)MgBr afforded cis-[Ni(PPh₃)₂Br(C₆H₂Me₂-3,5-OSiMe₃-4)] (3) that reacted with ⁿBu₄NF to yield [Ni(PPh₃)(C₆H₂Me₂-3,5-OH-4)]₂(μ-OH)₂ (4) containing a σ-bonded 4-hydroxyaryl ligand.

Original language	English
Pages (from-to)	1-4
Number of pages	4
Journal	Journal of Organometallic Chemistry
Volume	853
DOIs	https://doi.org/10.1016/j.jorganchem.2017.10.012
Publication status	Published - 15 Dec 2017

Bibliographical note

Publisher Copyright:
© 2017 Elsevier B.V.

Keywords

4-Hydroxyaryl complex
Group 10 metal
Phosphaquinone
Quinone

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10.1016/j.jorganchem.2017.10.012

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title = "4-Hydroxyaryl complexes of group 10 metals",

abstract = "Attempts have been made to synthesize group 10 metal complexes bearing σ-bonded 4-hydroxyaryl ligands that are potential precursors to metallaquinones. Treatment of 4-bromo-2,6-di-tert-butylphenol with [Pd(PPh3)4] led to formation of the phosphaquinone Ph3P = C6H3tBu2-3,5-O-4 (1), whereas that with [M(PPh3)4] (M = Ni, Pt) yielded the biquinone [C6H3tBu2-3,5-O-4]2 (2). The solid-state structure of 1 features a short C=O double bond and alternate phenyl C-C single and double bonds that are characteristic of quinoidal compounds. Alkylation of [NiCl2(PPh3)2] with (C6H2Me2-3,5-OSiMe3-4)MgBr afforded cis-[Ni(PPh3)2Br(C6H2Me2-3,5-OSiMe3-4)] (3) that reacted with nBu4NF to yield [Ni(PPh3)(C6H2Me2-3,5-OH-4)]2(μ-OH)2 (4) containing a σ-bonded 4-hydroxyaryl ligand.",

keywords = "4-Hydroxyaryl complex, Group 10 metal, Phosphaquinone, Quinone",

author = "So, \{Shiu Chun\} and Cheung, \{Wai Man\} and Sung, \{Herman H.Y.\} and Williams, \{Ian D.\} and Leung, \{Wa Hung\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier B.V.",

year = "2017",

month = dec,

day = "15",

doi = "10.1016/j.jorganchem.2017.10.012",

language = "English",

volume = "853",

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journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - 4-Hydroxyaryl complexes of group 10 metals

AU - So, Shiu Chun

AU - Cheung, Wai Man

AU - Sung, Herman H.Y.

AU - Williams, Ian D.

AU - Leung, Wa Hung

PY - 2017/12/15

Y1 - 2017/12/15

N2 - Attempts have been made to synthesize group 10 metal complexes bearing σ-bonded 4-hydroxyaryl ligands that are potential precursors to metallaquinones. Treatment of 4-bromo-2,6-di-tert-butylphenol with [Pd(PPh3)4] led to formation of the phosphaquinone Ph3P = C6H3tBu2-3,5-O-4 (1), whereas that with [M(PPh3)4] (M = Ni, Pt) yielded the biquinone [C6H3tBu2-3,5-O-4]2 (2). The solid-state structure of 1 features a short C=O double bond and alternate phenyl C-C single and double bonds that are characteristic of quinoidal compounds. Alkylation of [NiCl2(PPh3)2] with (C6H2Me2-3,5-OSiMe3-4)MgBr afforded cis-[Ni(PPh3)2Br(C6H2Me2-3,5-OSiMe3-4)] (3) that reacted with nBu4NF to yield [Ni(PPh3)(C6H2Me2-3,5-OH-4)]2(μ-OH)2 (4) containing a σ-bonded 4-hydroxyaryl ligand.

AB - Attempts have been made to synthesize group 10 metal complexes bearing σ-bonded 4-hydroxyaryl ligands that are potential precursors to metallaquinones. Treatment of 4-bromo-2,6-di-tert-butylphenol with [Pd(PPh3)4] led to formation of the phosphaquinone Ph3P = C6H3tBu2-3,5-O-4 (1), whereas that with [M(PPh3)4] (M = Ni, Pt) yielded the biquinone [C6H3tBu2-3,5-O-4]2 (2). The solid-state structure of 1 features a short C=O double bond and alternate phenyl C-C single and double bonds that are characteristic of quinoidal compounds. Alkylation of [NiCl2(PPh3)2] with (C6H2Me2-3,5-OSiMe3-4)MgBr afforded cis-[Ni(PPh3)2Br(C6H2Me2-3,5-OSiMe3-4)] (3) that reacted with nBu4NF to yield [Ni(PPh3)(C6H2Me2-3,5-OH-4)]2(μ-OH)2 (4) containing a σ-bonded 4-hydroxyaryl ligand.

KW - 4-Hydroxyaryl complex

KW - Group 10 metal

KW - Phosphaquinone

KW - Quinone

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000417654800001

UR - https://openalex.org/W2766372208

U2 - 10.1016/j.jorganchem.2017.10.012

DO - 10.1016/j.jorganchem.2017.10.012

M3 - Short survey

SN - 0022-328X

VL - 853

SP - 1

EP - 4

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

4-Hydroxyaryl complexes of group 10 metals

Abstract

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Keywords

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