Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed
enantioselective
arylation of both alkyl and aryl sulfenate anions to deliver various
chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities
(up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos).
PC-Phos are easily prepared in short steps from inexpensive commercially
available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered
ring was formed via the O,P-coordination with the palladium­(II) center.
The salient features of this method include general substrate scope,
ease of scale-up, applicable to the late-stage modification of bioactive
compounds, and the synthesis of a marketed medicine Sulindac.