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

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 previo...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-10, Vol.24 (57), p.15178-15184
Main Authors: Jones, Alexander W., Rank, Christian K., Becker, Yanik, Malchau, Christian, Funes‐Ardoiz, Ignacio, Maseras, Feliu, Patureau, Frederic W.
Format: Article
Language:English
Subjects:
Carbazoles
Chelates
Chemistry
Communication
Communications
Computer applications
cooperative reductive elimination
cross dehydrogenative coupling
C−H bond activation
Dehydrogenation
dehydrogenative amination
trinuclear catalysis
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Summary: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). Metals unite: 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. A decisive rate‐determining trinuclear Ru–Cu cooperative reductive elimination step (CRE) is described.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201802886