Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation: Modeling copper-monooxygenase C-H hydroxylation

Debabrata Maiti; Dong Heon Lee; Katya Gaoutchenova; Christian Würtele; Max C. Holthausen; Amy A. Narducci Sarjeant; Jörg Sundermeyer; Siegfried Schindler; Kenneth D. Karlin

doi:10.1002/anie.200704389

Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation: Modeling copper-monooxygenase C-H hydroxylation

Debabrata Maiti^*
, Dong Heon Lee
, Katya Gaoutchenova
, Christian Würtele
, Max C. Holthausen
, Amy A. Narducci Sarjeant
, Jörg Sundermeyer
, Siegfried Schindler
, Kenneth D. Karlin

^*Corresponding author for this work

Department of Chemistry

Johns Hopkins University
University of Marburg
Justus Liebig University Giessen
Goethe University Frankfurt

Research output: Contribution to journal › Journal article › peer-review

181 Scopus citations

Abstract

(Chemical Equation Presented) Donor makes the difference: The mononuclear η¹-superoxo copper(II) complex 1 undergoes dioxygen activation with the addition of hydrogen-atom donors. Net O₂-derived O-atom insertion into the N-methyl group of the ligand leads to formation of a copper(II)-alkoxide product 2. The cupric superoxo species 1 itself is not capable of the observed hydroxylation reaction.

Original language	English
Pages (from-to)	82-85
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	1
DOIs	https://doi.org/10.1002/anie.200704389
State	Published - 2008

Keywords

C-H activation
Copper
Hydroxylation
Oxo ligands
Superoxide ligands

Quacquarelli Symonds(QS) Subject Topics

Engineering - Petroleum
Engineering - Chemical
Chemistry

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10.1002/anie.200704389

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Maiti, D., Lee, D. H., Gaoutchenova, K., Würtele, C., Holthausen, M. C., Narducci Sarjeant, A. A., Sundermeyer, J., Schindler, S., & Karlin, K. D. (2008). Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation: Modeling copper-monooxygenase C-H hydroxylation. Angewandte Chemie - International Edition, 47(1), 82-85. https://doi.org/10.1002/anie.200704389

@article{152c436c8fa44e9382e6af507b905e68,

title = "Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation: Modeling copper-monooxygenase C-H hydroxylation",

abstract = "(Chemical Equation Presented) Donor makes the difference: The mononuclear η1-superoxo copper(II) complex 1 undergoes dioxygen activation with the addition of hydrogen-atom donors. Net O2-derived O-atom insertion into the N-methyl group of the ligand leads to formation of a copper(II)-alkoxide product 2. The cupric superoxo species 1 itself is not capable of the observed hydroxylation reaction.",

keywords = "C-H activation, Copper, Hydroxylation, Oxo ligands, Superoxide ligands",

author = "Debabrata Maiti and Lee, \{Dong Heon\} and Katya Gaoutchenova and Christian W{\"u}rtele and Holthausen, \{Max C.\} and \{Narducci Sarjeant\}, \{Amy A.\} and J{\"o}rg Sundermeyer and Siegfried Schindler and Karlin, \{Kenneth D.\}",

year = "2008",

doi = "10.1002/anie.200704389",

language = "English",

volume = "47",

pages = "82--85",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

number = "1",

}

Maiti, D, Lee, DH, Gaoutchenova, K, Würtele, C, Holthausen, MC, Narducci Sarjeant, AA, Sundermeyer, J, Schindler, S & Karlin, KD 2008, 'Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation: Modeling copper-monooxygenase C-H hydroxylation', Angewandte Chemie - International Edition, vol. 47, no. 1, pp. 82-85. https://doi.org/10.1002/anie.200704389

TY - JOUR

T1 - Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation

T2 - Modeling copper-monooxygenase C-H hydroxylation

AU - Maiti, Debabrata

AU - Lee, Dong Heon

AU - Gaoutchenova, Katya

AU - Würtele, Christian

AU - Holthausen, Max C.

AU - Narducci Sarjeant, Amy A.

AU - Sundermeyer, Jörg

AU - Schindler, Siegfried

AU - Karlin, Kenneth D.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Donor makes the difference: The mononuclear η1-superoxo copper(II) complex 1 undergoes dioxygen activation with the addition of hydrogen-atom donors. Net O2-derived O-atom insertion into the N-methyl group of the ligand leads to formation of a copper(II)-alkoxide product 2. The cupric superoxo species 1 itself is not capable of the observed hydroxylation reaction.

AB - (Chemical Equation Presented) Donor makes the difference: The mononuclear η1-superoxo copper(II) complex 1 undergoes dioxygen activation with the addition of hydrogen-atom donors. Net O2-derived O-atom insertion into the N-methyl group of the ligand leads to formation of a copper(II)-alkoxide product 2. The cupric superoxo species 1 itself is not capable of the observed hydroxylation reaction.

KW - C-H activation

KW - Copper

KW - Hydroxylation

KW - Oxo ligands

KW - Superoxide ligands

UR - https://www.scopus.com/pages/publications/37549045624

U2 - 10.1002/anie.200704389

DO - 10.1002/anie.200704389

M3 - Journal article

C2 - 18022887

AN - SCOPUS:37549045624

SN - 1433-7851

VL - 47

SP - 82

EP - 85

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 1

ER -

Reactions of a copper(II) superoxo complex lead to C-H and O-H substrate oxygenation: Modeling copper-monooxygenase C-H hydroxylation

Abstract

Keywords

Quacquarelli Symonds(QS) Subject Topics

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