Dioxygen activation by an organometallic Pd(ii) precursor: formation of a Pd(iv)-OH complex and its C-O bond formation reactivity

Fengrui Qu; Julia R. Khusnutdinova; Nigam P. Rath; Liviu M. Mirica

doi:10.1039/c3cc49387c

Dioxygen activation by an organometallic Pd(ii) precursor: formation of a Pd(iv)-OH complex and its C-O bond formation reactivity

Fengrui Qu, Julia R. Khusnutdinova, Nigam P. Rath, Liviu M. Mirica

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Abstract

The complex (Me₃tacn)Pd^II(CH₂CMe₂C₆H₄) is readily oxidized by O₂ or H₂O₂ to yield the Pd^IV-OH complex [(Me₃tacn)Pd^IV(OH)(CH₂CMe₂C₆H₄)]⁺. Thermolysis of this product leads to the selective C(sp²)-O reductive elimination of 2-tert-butylphenol, no C(sp³)-O elimination product being detected. This system represents a rare example of selective C(sp²)-O bond formation that is relevant to Pd-catalyzed aerobic C-H hydroxylation reactions.

Original language	English
Pages (from-to)	3036-3039
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	23
DOIs	https://doi.org/10.1039/c3cc49387c
State	Published - Feb 20 2014

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abstract = "The complex (Me3tacn)PdII(CH2CMe2C6H4) is readily oxidized by O2 or H2O2 to yield the PdIV-OH complex [(Me3tacn)PdIV(OH)(CH2CMe2C6H4)]+. Thermolysis of this product leads to the selective C(sp2)-O reductive elimination of 2-tert-butylphenol, no C(sp3)-O elimination product being detected. This system represents a rare example of selective C(sp2)-O bond formation that is relevant to Pd-catalyzed aerobic C-H hydroxylation reactions.",

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T1 - Dioxygen activation by an organometallic Pd(ii) precursor

T2 - formation of a Pd(iv)-OH complex and its C-O bond formation reactivity

AU - Qu, Fengrui

AU - Khusnutdinova, Julia R.

AU - Rath, Nigam P.

AU - Mirica, Liviu M.

PY - 2014/2/20

Y1 - 2014/2/20

N2 - The complex (Me3tacn)PdII(CH2CMe2C6H4) is readily oxidized by O2 or H2O2 to yield the PdIV-OH complex [(Me3tacn)PdIV(OH)(CH2CMe2C6H4)]+. Thermolysis of this product leads to the selective C(sp2)-O reductive elimination of 2-tert-butylphenol, no C(sp3)-O elimination product being detected. This system represents a rare example of selective C(sp2)-O bond formation that is relevant to Pd-catalyzed aerobic C-H hydroxylation reactions.

AB - The complex (Me3tacn)PdII(CH2CMe2C6H4) is readily oxidized by O2 or H2O2 to yield the PdIV-OH complex [(Me3tacn)PdIV(OH)(CH2CMe2C6H4)]+. Thermolysis of this product leads to the selective C(sp2)-O reductive elimination of 2-tert-butylphenol, no C(sp3)-O elimination product being detected. This system represents a rare example of selective C(sp2)-O bond formation that is relevant to Pd-catalyzed aerobic C-H hydroxylation reactions.

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DO - 10.1039/c3cc49387c

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VL - 50

SP - 3036

EP - 3039

JO - Chemical Communications

JF - Chemical Communications

IS - 23

ER -

Dioxygen activation by an organometallic Pd(ii) precursor: formation of a Pd(iv)-OH complex and its C-O bond formation reactivity

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