title: Directed Metalation-Suzuki-Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes.
abstract: A general, efficient, and regioselective synthesis of a series of hydroxylated 1-methylphenanthrenes 9 by a combined directed ortho metalation (DoM)-Suzuki-Miyaura cross-coupling-directed remote metalation (DreM) sequence is reported. Diversity to this methodology was achieved by a regioselective DoM rather than DreM reaction, affording more highly substituted phenanthrols ( Table 2 ). Application of the turbo-Grignard reagent (i-PrMgCl·LiCl) in the Ni-catalyzed Corriu-Kumada reaction gave efficient decarbamoylation ( Tables 3 and 4 ). Additional features are the TMS protecting group and halo-induced ipso-desilylation tactics applied to the regioselective synthesis of phenanthrenes ( Scheme 2 ).
authors: Faculty of Science and Technology, University of Stavanger , N-4036 Stavanger, Norway.
authors: Kåre B
authors: KB
authors: Jørgensen
authors: Snieckus Innovations and Department of Chemistry, Queen's University , Kingston, ON, Canada K7L 3N6.
authors: Toni
authors: T
authors: Rantanen
authors: Snieckus Innovations and Department of Chemistry, Queen's University , Kingston, ON, Canada K7L 3N6.
authors: Thilo
authors: T
authors: Dörfler
authors: Snieckus Innovations and Department of Chemistry, Queen's University , Kingston, ON, Canada K7L 3N6.
authors: Victor
authors: V
authors: Snieckus