Nature of the copper-oxide-mediated C-S cross-coupling reaction

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Nature of the copper-oxide-mediated C-S cross-coupling reaction : Leaching of catalytically active species from the metal oxide surface. / Panova, Yulia S.; Kashin, Alexey S.; Vorobev, Maxim G.; Degtyareva, Evgeniya S.; Ananikov, Valentine P.

In: ACS Catalysis, Vol. 6, No. 6, 03.06.2016, p. 3637-3643.

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

Author

Panova, Yulia S. ; Kashin, Alexey S. ; Vorobev, Maxim G. ; Degtyareva, Evgeniya S. ; Ananikov, Valentine P. / Nature of the copper-oxide-mediated C-S cross-coupling reaction : Leaching of catalytically active species from the metal oxide surface. In: ACS Catalysis. 2016 ; Vol. 6, No. 6. pp. 3637-3643.

BibTeX

@article{12aab1dbab6a4aafb799d631cf5030fa,

title = "Nature of the copper-oxide-mediated C-S cross-coupling reaction: Leaching of catalytically active species from the metal oxide surface",

abstract = "Copper-oxide-catalyzed cross-coupling reaction is a well-known strategy in heterogeneous catalysis. A large number of applications have been developed, and catalytic cycles have been proposed based on the involvement of the copper oxide surface. In the present work, we have demonstrated that copper(I) and copper(II) oxides served as precursors in the coupling reaction between thiols and aryl halides, while catalytically active species were formed upon unusual leaching from the oxide surface. A powerful cryo-SEM technique has been utilized to characterize the solution-state catalytic system by electron microscopy. A series of different experimental methods were used to reveal the key role of copper thiolate intermediates in the studied catalytic reaction. The present study shows an example of leaching from a metal oxide surface, where the leaching process involved the formation of a metal thiolate and the release of water. A new synthetic approach was developed, and many functionalized sulfides were synthesized with yields of up to 96%, using the copper thiolate catalyst. The study suggests that metal oxides may not act as an innocent material under reaction conditions; rather, they may represent a source of reactive species for solution-state homogeneous catalysis.",

keywords = "C-S cross-coupling, catalysis, copper oxide, leaching, mechanism, nanoparticles",

author = "Panova, {Yulia S.} and Kashin, {Alexey S.} and Vorobev, {Maxim G.} and Degtyareva, {Evgeniya S.} and Ananikov, {Valentine P.}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = jun,

day = "3",

doi = "10.1021/acscatal.6b00337",

language = "English",

volume = "6",

pages = "3637--3643",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "6",

}

RIS

TY - JOUR

T1 - Nature of the copper-oxide-mediated C-S cross-coupling reaction

T2 - Leaching of catalytically active species from the metal oxide surface

AU - Panova, Yulia S.

AU - Kashin, Alexey S.

AU - Vorobev, Maxim G.

AU - Degtyareva, Evgeniya S.

AU - Ananikov, Valentine P.

PY - 2016/6/3

Y1 - 2016/6/3

N2 - Copper-oxide-catalyzed cross-coupling reaction is a well-known strategy in heterogeneous catalysis. A large number of applications have been developed, and catalytic cycles have been proposed based on the involvement of the copper oxide surface. In the present work, we have demonstrated that copper(I) and copper(II) oxides served as precursors in the coupling reaction between thiols and aryl halides, while catalytically active species were formed upon unusual leaching from the oxide surface. A powerful cryo-SEM technique has been utilized to characterize the solution-state catalytic system by electron microscopy. A series of different experimental methods were used to reveal the key role of copper thiolate intermediates in the studied catalytic reaction. The present study shows an example of leaching from a metal oxide surface, where the leaching process involved the formation of a metal thiolate and the release of water. A new synthetic approach was developed, and many functionalized sulfides were synthesized with yields of up to 96%, using the copper thiolate catalyst. The study suggests that metal oxides may not act as an innocent material under reaction conditions; rather, they may represent a source of reactive species for solution-state homogeneous catalysis.

AB - Copper-oxide-catalyzed cross-coupling reaction is a well-known strategy in heterogeneous catalysis. A large number of applications have been developed, and catalytic cycles have been proposed based on the involvement of the copper oxide surface. In the present work, we have demonstrated that copper(I) and copper(II) oxides served as precursors in the coupling reaction between thiols and aryl halides, while catalytically active species were formed upon unusual leaching from the oxide surface. A powerful cryo-SEM technique has been utilized to characterize the solution-state catalytic system by electron microscopy. A series of different experimental methods were used to reveal the key role of copper thiolate intermediates in the studied catalytic reaction. The present study shows an example of leaching from a metal oxide surface, where the leaching process involved the formation of a metal thiolate and the release of water. A new synthetic approach was developed, and many functionalized sulfides were synthesized with yields of up to 96%, using the copper thiolate catalyst. The study suggests that metal oxides may not act as an innocent material under reaction conditions; rather, they may represent a source of reactive species for solution-state homogeneous catalysis.

KW - C-S cross-coupling

KW - catalysis

KW - copper oxide

KW - leaching

KW - mechanism

KW - nanoparticles

UR - http://www.scopus.com/inward/record.url?scp=84973647690&partnerID=8YFLogxK

U2 - 10.1021/acscatal.6b00337

DO - 10.1021/acscatal.6b00337

M3 - Article

AN - SCOPUS:84973647690

VL - 6

SP - 3637

EP - 3643

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 6

ER -

ID: 100699510