Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki-Miyaura Cross-Coupling in Water and Air

J Org Chem. 2018 Dec 21;83(24):15486-15492. doi: 10.1021/acs.joc.8b02340. Epub 2018 Dec 5.

Abstract

With use of a Pd(II)-sulfosalan complex as a water-soluble catalyst, we have developed an efficient synthesis of biaryls via Suzuki-Miyaura cross-coupling in water under aerobic conditions. The water-insoluble target molecules were isolated by simple filtration in analytical purity after washing with 0.01 M aqueous HCl (20 examples). In most cases, palladium contamination was below 5 ppm considered acceptable for active pharmaceutical ingredients. The established method is scalable, reproducible, and provides biaryl products in isolated yields up to 91%.

Publication types

  • Research Support, Non-U.S. Gov't