Combined directed ortho Metalation/Suzuki-Miyaura cross-coupling strategies. Regiospecific synthesis of chlorodihydroxybiphenyls and polychlorinated biphenyls.
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.
Nerdinger
S
S
Sandoz GmbH, ATKU, B104/6/R703, Sandoz GmbH, Biochemiestrasse 10, A-6250 Kundl/Tirol, Austria.
Kendall
C
C
Cai
X
X
Marchart
R
R
Riebel
P
P
Johnson
M R
MR
Yin
C-F
CF
Hénaff
N
N
Eltis
L D
LD
Snieckus
V
V
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
D001713:Biphenyl Compounds; D002396:Catechols; D007202:Indicators and Reagents; C074625:1,2-dihydroxy-4'-chlorobiphenyl; D011078:Polychlorinated Biphenyls