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

• Published in: Angewandte 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
• Language: English
• Published: Germany Wiley Subscription Services, Inc 20-11-2017
• Edition: International 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
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201708271

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.