title: Beyond Directed ortho Metalation: Ruthenium-Catalyzed Amide-Directed CAr-OMe Activation/Cross-Coupling Reaction of Naphthamides with Aryl Boronates.
abstract: A new and general synthetic methodology for the construction of biaryl, heterobiaryl, and polyaryl molecules by the ruthenium-catalyzed cross-coupling of ortho-methoxy naphthamides with aryl boroneopentylates is described. The isomeric 1-MeO-2-naphthamides and 2-MeO-1-naphthamides furnish an expansive series of arylated naphthamides in excellent yields. Competition experiments showed the higher reactivity of 1-MeO-2-naphthamide over 2-MeO-benzamide. Orthogonality between the C-O activation/cross-coupling and the Suzuki-Miyaura reactions was established. The method provides naphthalenes which are difficult to prepare by directed ortho metalation.
authors.affiliation: Department of Chemistry, Queen's University , 90 Bader Lane, Kingston, ON K7L 3N6, Canada.
authors.forename: Yigang
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, Queen's University , 90 Bader Lane, Kingston, ON K7L 3N6, Canada.
authors.forename: Victor
authors.initials: V
authors.lastname: Snieckus