Aromatic hydroxylation reactivity of a mononuclear Cu(II)-alkylperoxo complex

Atsushi Kunishita; Junji Teraoka; Joseph D. Scanlon; Takahiro Matsumoto; Masatatsu Suzuki; Christopher J. Cramer; Shinobu Itoh

doi:10.1021/ja071623g

Aromatic hydroxylation reactivity of a mononuclear Cu(II)-alkylperoxo complex

Atsushi Kunishita, Junji Teraoka, Joseph D. Scanlon, Takahiro Matsumoto, Masatatsu Suzuki, Christopher J. Cramer, Shinobu Itoh

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

43 Scopus citations

Abstract

Reaction of copper(II) complex 1^X supported by the tridentate bis(pyridylmethyl)amine ligand containing m-substituted phenyl groups at the 6-positions of the pyridine rings (L^X) with H₂O₂ in the presence of triethylamine (NEt₃) in acetone generates a copper(II)-alkylperoxo species 2^X [2-hydroxy-2-hydroperoxypropane (HHPP) adduct]. The alkylperoxo intermediate 2^X undergoes an efficient aromatic ligand hydroxylation reaction, producing a phenolate complex 4^X via another intermediate 3^X. Kinetic studies on the aromatic hydroxylation process are reported together with spectral characterization of 2^X.

Original language	English (US)
Pages (from-to)	7248-7249
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	23
DOIs	https://doi.org/10.1021/ja071623g
State	Published - Jun 13 2007
Externally published	Yes

Access

10.1021/ja071623g

OpenUrl availability

Full text

Cite this

@article{f7865bc2fd634c639c6ee6950c8a0dd3,

title = "Aromatic hydroxylation reactivity of a mononuclear Cu(II)-alkylperoxo complex",

abstract = "Reaction of copper(II) complex 1X supported by the tridentate bis(pyridylmethyl)amine ligand containing m-substituted phenyl groups at the 6-positions of the pyridine rings (LX) with H2O2 in the presence of triethylamine (NEt3) in acetone generates a copper(II)-alkylperoxo species 2X [2-hydroxy-2-hydroperoxypropane (HHPP) adduct]. The alkylperoxo intermediate 2X undergoes an efficient aromatic ligand hydroxylation reaction, producing a phenolate complex 4X via another intermediate 3X. Kinetic studies on the aromatic hydroxylation process are reported together with spectral characterization of 2X.",

author = "Atsushi Kunishita and Junji Teraoka and Scanlon, {Joseph D.} and Takahiro Matsumoto and Masatatsu Suzuki and Cramer, {Christopher J.} and Shinobu Itoh",

year = "2007",

month = jun,

day = "13",

doi = "10.1021/ja071623g",

language = "English (US)",

volume = "129",

pages = "7248--7249",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Aromatic hydroxylation reactivity of a mononuclear Cu(II)-alkylperoxo complex

AU - Kunishita, Atsushi

AU - Teraoka, Junji

AU - Scanlon, Joseph D.

AU - Matsumoto, Takahiro

AU - Suzuki, Masatatsu

AU - Cramer, Christopher J.

AU - Itoh, Shinobu

PY - 2007/6/13

Y1 - 2007/6/13

N2 - Reaction of copper(II) complex 1X supported by the tridentate bis(pyridylmethyl)amine ligand containing m-substituted phenyl groups at the 6-positions of the pyridine rings (LX) with H2O2 in the presence of triethylamine (NEt3) in acetone generates a copper(II)-alkylperoxo species 2X [2-hydroxy-2-hydroperoxypropane (HHPP) adduct]. The alkylperoxo intermediate 2X undergoes an efficient aromatic ligand hydroxylation reaction, producing a phenolate complex 4X via another intermediate 3X. Kinetic studies on the aromatic hydroxylation process are reported together with spectral characterization of 2X.

AB - Reaction of copper(II) complex 1X supported by the tridentate bis(pyridylmethyl)amine ligand containing m-substituted phenyl groups at the 6-positions of the pyridine rings (LX) with H2O2 in the presence of triethylamine (NEt3) in acetone generates a copper(II)-alkylperoxo species 2X [2-hydroxy-2-hydroperoxypropane (HHPP) adduct]. The alkylperoxo intermediate 2X undergoes an efficient aromatic ligand hydroxylation reaction, producing a phenolate complex 4X via another intermediate 3X. Kinetic studies on the aromatic hydroxylation process are reported together with spectral characterization of 2X.

UR - http://www.scopus.com/inward/record.url?scp=34250792279&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34250792279&partnerID=8YFLogxK

U2 - 10.1021/ja071623g

DO - 10.1021/ja071623g

M3 - Article

C2 - 17503824

AN - SCOPUS:34250792279

SN - 0002-7863

VL - 129

SP - 7248

EP - 7249

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 23

ER -

Aromatic hydroxylation reactivity of a mononuclear Cu(II)-alkylperoxo complex

Abstract

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this