Direct Benzene Hydroxylation with Dioxygen Induced by Copper Complexes: Uncovering the Active Species by DFT Calculations

Agusti Lledos Falco; Laura Tiessler Sala; Jesús J. Lázaro; Elena Borrego; Ana Caballero; Pedro J. Pérez

Direct Benzene Hydroxylation with Dioxygen Induced by Copper Complexes: Uncovering the Active Species by DFT Calculations

Agusti Lledos Falco, Laura Tiessler Sala, Jesús J. Lázaro, Elena Borrego, Ana Caballero, Pedro J. Pérez

Cepsa Research Center, Compañía Española de Petróleos S.A.,
Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva

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Resum

The direct oxidation of benzene into phenol using
molecular oxygen at very mild temperatures can be promoted in the
presence of the copper complex Tp^Br3Cu(NCMe) in the homogeneous
phase in the presence of ascorbic acid as the source of protons and
electrons. The stoichiometric nature, relative to copper, of this
transformation prompted a thorough DFT study in order to understand
the reaction pathway. As a result, the dinuclear species Tp^Br3CuII(μ-O•)(μ-OH)Cu^IITp^Br3is proposed as the relevant structure which
is responsible for activating the arene C−H bond leading to phenol formation.

Idioma original	Anglès
Pàgines (de-a)	1892−1904
Nombre de pàgines	13
Revista	Organometallics
Volum	41
Número	14
Estat de la publicació	Publicada - 14 de jul. 2022

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@article{50a52821515c4987a36753fd3ff54385,

title = "Direct Benzene Hydroxylation with Dioxygen Induced by Copper Complexes: Uncovering the Active Species by DFT Calculations",

abstract = "The direct oxidation of benzene into phenol usingmolecular oxygen at very mild temperatures can be promoted in thepresence of the copper complex TpBr3Cu(NCMe) in the homogeneousphase in the presence of ascorbic acid as the source of protons andelectrons. The stoichiometric nature, relative to copper, of thistransformation prompted a thorough DFT study in order to understandthe reaction pathway. As a result, the dinuclear species TpBr3CuII(μ-O•)(μ-OH)CuIITpBr3 is proposed as the relevant structure whichis responsible for activating the arene C−H bond leading to phenol formation.",

keywords = "Benzene hydroxylation - dioxygen - copper - DFT",

author = "{Lledos Falco}, Agusti and {Tiessler Sala}, Laura and L{\'a}zaro, {Jes{\'u}s J.} and Elena Borrego and Ana Caballero and P{\'e}rez, {Pedro J.}",

year = "2022",

month = jul,

day = "14",

language = "English",

volume = "41",

pages = "1892−1904",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Direct Benzene Hydroxylation with Dioxygen Induced by Copper Complexes: Uncovering the Active Species by DFT Calculations

AU - Lledos Falco, Agusti

AU - Tiessler Sala, Laura

AU - Lázaro, Jesús J.

AU - Borrego, Elena

AU - Caballero, Ana

AU - Pérez, Pedro J.

PY - 2022/7/14

Y1 - 2022/7/14

N2 - The direct oxidation of benzene into phenol usingmolecular oxygen at very mild temperatures can be promoted in thepresence of the copper complex TpBr3Cu(NCMe) in the homogeneousphase in the presence of ascorbic acid as the source of protons andelectrons. The stoichiometric nature, relative to copper, of thistransformation prompted a thorough DFT study in order to understandthe reaction pathway. As a result, the dinuclear species TpBr3CuII(μ-O•)(μ-OH)CuIITpBr3 is proposed as the relevant structure whichis responsible for activating the arene C−H bond leading to phenol formation.

AB - The direct oxidation of benzene into phenol usingmolecular oxygen at very mild temperatures can be promoted in thepresence of the copper complex TpBr3Cu(NCMe) in the homogeneousphase in the presence of ascorbic acid as the source of protons andelectrons. The stoichiometric nature, relative to copper, of thistransformation prompted a thorough DFT study in order to understandthe reaction pathway. As a result, the dinuclear species TpBr3CuII(μ-O•)(μ-OH)CuIITpBr3 is proposed as the relevant structure whichis responsible for activating the arene C−H bond leading to phenol formation.

KW - Benzene hydroxylation - dioxygen - copper - DFT

M3 - Article

C2 - 35936655

SN - 0276-7333

VL - 41

SP - 1892−1904

JO - Organometallics

JF - Organometallics

IS - 14

ER -

Direct Benzene Hydroxylation with Dioxygen Induced by Copper Complexes: Uncovering the Active Species by DFT Calculations

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