Improvement in the Palladium-Catalyzed Miyaura Borylation Reaction by Optimization of the Base: Scope and Mechanistic Study
Santiago Barroso, Markus Joksch, Pim Puylaert, Sergey Tin, Stephen J. Bell, Luke Donnellan, Stewart Duguid, Colin Muir, Peichao Zhao, Vittorio Farina, Duc N. Tran* and Johannes G. de Vries*
*Janssen Pharmaceutica, 2340 Beerse, Belgium; Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock, Germany,
Email: ntran25
its.jnj.com, johannes.devriescatalysis.de
S. Barroso, M. Joksch, P. Puylaert, S. Tin, S. J. Bell, L. Donnellan, S. Duguid, C. Muir, P. Zhao, V. Farina, D. N. Tran, J. G. de Vries, J. Org. Chem., 2021, 86, 103-109.
DOI: 10.1021/acs.joc.0c01758
see article for more reactions
Abstract
By using lipophilic bases such as potassium 2-ethyl hexanoate, the palladium-catalyzed Suzuki-Miyaura borylation of a wide range of substrates could be achieved at 35°C in less than 2 h with very low catalyst loading. A mechanistic study shows a hitherto unrecognized inhibitory effect by the acetate anion on the catalytic cycle, whereas use of bulky 2-ethyl hexanoate minimizes this inhibitory effect.
see article for more examples
Inhibitory effect of acetate
Key Words
Miyaura Borylation, Arylboronates
ID: J42-Y2021
