Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination.

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Synthesis of Axially Chiral Olefin-Oxazoline Ligands via Pd-Catalyzed Multiple C-H Functionalization.

We report herein the Pd-catalyzed oxazoline-directed C-H olefination of the N-arylindole skeleton, affording two diastereomers of axially chiral olefin-oxazoline ligands in a one-step procedure. Modifications at the 3- and 3'-positions were facilely achieved via electrophilic substitution of the indole fragment and subsequent oxazoline-directed C-H amidation or olefination of the arene fragment.