Preparative Scale Synthesis of the Biaryl Core of Anacetrapib via a Ruthenium-Catalyzed Direct Arylation Reaction: Unexpected Effect of Solvent Impurity on the Arylation Reaction

作者:Ouellet Stephane G*; Roy Amelie; Molinaro Carmela; Angelaud Remy; Marcoux Jean Francois; O'Shea Paul D; Davies Ian W
来源:Journal of Organic Chemistry, 2011, 76(5): 1436-1439.
DOI:10.1021/jo1018574

摘要

In this report, we disclose our findings regarding the remarkable effect of a low-level impurity found in the solvent used for a ruthenium-catalyzed direct arylation reaction. This discovery allowed for the development of a robust and high-yield arylation protocol that was demonstrated on a multi-kilogram scale using carboxylate as the cocatalyst. Finally, a practical, scalable, and chromatography-free synthesis of the biaryl core of Anacetrapib is described.

  • 出版日期2011-3-4