title: Combined directed ortho Metalation/Suzuki-Miyaura cross-coupling strategies. Regiospecific synthesis of chlorodihydroxybiphenyls and polychlorinated biphenyls.
abstract: The Directed ortho Metalation (DoM)/Suzuki-Miyaura cross-coupling strategy is applied for the regiospecific construction of all isomeric monochloro and selected dichloro and trichloro 2,3-dihydroxybiphenyls (DHBs). The combined methodology highlights iterative DoM processes, hindered Suzuki-Miyaura couplings, and advantages in diversity in approaches from commercial starting materials leading to provision of chloro-DHBs as single isomers in high purity and on a gram scale. The syntheis of several PCBs are also reported.
authors.affiliation: Sandoz GmbH, ATKU, B104/6/R703, Sandoz GmbH, Biochemiestrasse 10, A-6250 Kundl/Tirol, Austria.
authors.forename: S
authors.initials: S
authors.lastname: Nerdinger
authors.forename: C
authors.initials: C
authors.lastname: Kendall
authors.forename: X
authors.initials: X
authors.lastname: Cai
authors.forename: R
authors.initials: R
authors.lastname: Marchart
authors.forename: P
authors.initials: P
authors.lastname: Riebel
authors.forename: M R
authors.initials: MR
authors.lastname: Johnson
authors.forename: C-F
authors.initials: CF
authors.lastname: Yin
authors.forename: N
authors.initials: N
authors.lastname: Hénaff
authors.forename: L D
authors.initials: LD
authors.lastname: Eltis
authors.forename: V
authors.initials: V
authors.lastname: Snieckus
mesh_terms: D001713:Biphenyl Compounds / Q000138:chemical synthesis*; D002396:Catechols / Q000138:chemical synthesis*; D002625:Chemistry, Organic / Q000379:methods*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011078:Polychlorinated Biphenyls / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001713:Biphenyl Compounds; D002396:Catechols; D007202:Indicators and Reagents; C074625:1,2-dihydroxy-4'-chlorobiphenyl; D011078:Polychlorinated Biphenyls