Accelerated Ru–Cu Trinuclear Cooperative C−H Bond Functionalization of Carbazoles: A Kinetic and Computational Investigation

Alexander W. Jones; Christian K. Rank; Yanik Becker; Christian Malchau; Ignacio Funes-Ardoiz; Feliu Maseras; Frederic W. Patureau

doi:10.1002/chem.201802886

Accelerated Ru–Cu Trinuclear Cooperative C−H Bond Functionalization of Carbazoles: A Kinetic and Computational Investigation

Alexander W. Jones, Christian K. Rank, Yanik Becker, Christian Malchau, Ignacio Funes-Ardoiz, Feliu Maseras, Frederic W. Patureau

Department of Chemistry

Research output: Contribution to journal › Article › Research

5 Citations (Scopus)

Abstract

© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. The mechanism of a trinuclear cooperative dehydrogenative C−N bond-forming reaction is investigated in this work, which avoids the use of chelate-assisting directing groups. Two new highly efficient Ru/Cu co-catalyzed systems were identified, allowing orders of magnitude greater TOFs than the previous state of the art. In-depth kinetic studies were performed in combination with advanced DFT calculations, which reveal a decisive rate-determining trinuclear Ru–Cu cooperative reductive elimination step (CRE).

Original language	English
Pages (from-to)	15178-15184
Journal	Chemistry - A European Journal
Volume	24
DOIs	https://doi.org/10.1002/chem.201802886
Publication status	Published - 12 Oct 2018

Keywords

cooperative reductive elimination
cross dehydrogenative coupling
C−H bond activation
dehydrogenative amination
trinuclear catalysis

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title = "Accelerated Ru–Cu Trinuclear Cooperative C−H Bond Functionalization of Carbazoles: A Kinetic and Computational Investigation",

abstract = "{\textcopyright} 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. The mechanism of a trinuclear cooperative dehydrogenative C−N bond-forming reaction is investigated in this work, which avoids the use of chelate-assisting directing groups. Two new highly efficient Ru/Cu co-catalyzed systems were identified, allowing orders of magnitude greater TOFs than the previous state of the art. In-depth kinetic studies were performed in combination with advanced DFT calculations, which reveal a decisive rate-determining trinuclear Ru–Cu cooperative reductive elimination step (CRE).",

keywords = "cooperative reductive elimination, cross dehydrogenative coupling, C−H bond activation, dehydrogenative amination, trinuclear catalysis",

author = "Jones, {Alexander W.} and Rank, {Christian K.} and Yanik Becker and Christian Malchau and Ignacio Funes-Ardoiz and Feliu Maseras and Patureau, {Frederic W.}",

year = "2018",

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day = "12",

doi = "10.1002/chem.201802886",

language = "English",

volume = "24",

pages = "15178--15184",

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Accelerated Ru–Cu Trinuclear Cooperative C−H Bond Functionalization of Carbazoles: A Kinetic and Computational Investigation. / Jones, Alexander W.; Rank, Christian K.; Becker, Yanik; Malchau, Christian; Funes-Ardoiz, Ignacio; Maseras, Feliu; Patureau, Frederic W.

In: Chemistry - A European Journal, Vol. 24, 12.10.2018, p. 15178-15184.

Research output: Contribution to journal › Article › Research

TY - JOUR

T1 - Accelerated Ru–Cu Trinuclear Cooperative C−H Bond Functionalization of Carbazoles: A Kinetic and Computational Investigation

AU - Jones, Alexander W.

AU - Rank, Christian K.

AU - Becker, Yanik

AU - Malchau, Christian

AU - Funes-Ardoiz, Ignacio

AU - Maseras, Feliu

AU - Patureau, Frederic W.

PY - 2018/10/12

Y1 - 2018/10/12

N2 - © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. The mechanism of a trinuclear cooperative dehydrogenative C−N bond-forming reaction is investigated in this work, which avoids the use of chelate-assisting directing groups. Two new highly efficient Ru/Cu co-catalyzed systems were identified, allowing orders of magnitude greater TOFs than the previous state of the art. In-depth kinetic studies were performed in combination with advanced DFT calculations, which reveal a decisive rate-determining trinuclear Ru–Cu cooperative reductive elimination step (CRE).

AB - © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. The mechanism of a trinuclear cooperative dehydrogenative C−N bond-forming reaction is investigated in this work, which avoids the use of chelate-assisting directing groups. Two new highly efficient Ru/Cu co-catalyzed systems were identified, allowing orders of magnitude greater TOFs than the previous state of the art. In-depth kinetic studies were performed in combination with advanced DFT calculations, which reveal a decisive rate-determining trinuclear Ru–Cu cooperative reductive elimination step (CRE).

KW - cooperative reductive elimination

KW - cross dehydrogenative coupling

KW - C−H bond activation

KW - dehydrogenative amination

KW - trinuclear catalysis

U2 - 10.1002/chem.201802886

DO - 10.1002/chem.201802886

M3 - Article

C2 - 29928784

VL - 24

SP - 15178

EP - 15184

ER -