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We have optimized the Pd-catalyzed intramolecular α-arylation of 2-(2-halo-benzyl)-cyclohexanones and found that the use of 2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (X-Phos) as an added ligand led to a reproducible, efficient, and scalable synthesis of tricycle-[7.3.1.02,7]-trideca-2,4,6-trien-13-ones.

A robust method has been developed to couple a wide variety of pyridin-2-ones and aryl halides. This C–N bond forming reaction makes use of catalytic copper(I) iodide and the ligand 8-hydroxyquinoline. These conditions tolerate a wide degree of functionality on both the aryl halide and pyridin-2-one reactants and have resulted in numerous examples being synthesized.

A small molecule factor VIIa inhibitor has recently been reported by the Ono Pharmaceutical Company. Herein, we outline an efficient and convergent, synthetic route that relies upon a palladium-catalyzed Stille coupling reaction as a key step for the synthesis of the inhibitor.