Synergistic Manganese(I) C−H Activation Catalysis in Continuous Flow: Chemoselective Hydroarylation

Chemoselective hydroarylations were accomplished by a novel synergistic Brønsted acid/manganese(I)‐catalyzed C−H activation manifold. Thus, alkynes bearing O‐leaving groups could, for the first time, be employed for C−H alkenylations without concurrent β‐O elimination, thereby setting the stage for...

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Published inAngewandte Chemie International Edition Vol. 56; no. 47; pp. 15063 - 15067
Main Authors Wang, Hui, Pesciaioli, Fabio, Oliveira, João C. A., Warratz, Svenja, Ackermann, Lutz
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 20.11.2017
EditionInternational ed. in English
Subjects
Activation
Alkynes
Catalysis
Continuous flow
C−H activation
flow chemistry
heterocycles
Manganese
reaction mechanisms
reaction mechanisms
C−H activation
heterocycles
manganese
flow chemistry
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Summary:Chemoselective hydroarylations were accomplished by a novel synergistic Brønsted acid/manganese(I)‐catalyzed C−H activation manifold. Thus, alkynes bearing O‐leaving groups could, for the first time, be employed for C−H alkenylations without concurrent β‐O elimination, thereby setting the stage for versatile late‐stage diversifications. Also described is the first manganese‐catalyzed C−H activation in continuous flow, thus enabling efficient hydroarylations within only 20 minutes. Mn with the flow: Synergistic Brønsted acid/manganese(I) catalysis enables chemoselective hydroarylations, in flow, within 1 to 20 minutes, and sets the stage for versatile late‐stage modifications. The reaction features facile C−H cleavage and the use of nontoxic sustainable manganese.
Bibliography:These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201708271