38444-88-1Relevant articles and documents
Combined Directed ortho Metalation/Suzuki-Miyaura cross-coupling strategies. Regiospecific synthesis of chlorodihydroxybiphenyls and polychlorinated biphenyls
Nerdinger,Kendall,Cai,Marchart,Riebel,Johnson,Yin,Henaff,Eltis,Snieckus
, p. 5960 - 5967 (2008/02/09)
(Chemical Equation Presented) 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.
Synthesis of polychlorinated biphenyls (PCBs) using the Suzuki-coupling
Lehmler, Hans-Joachim,Robertson, Larry W
, p. 137 - 143 (2007/10/03)
An improved synthesis of polychlorinated biphenyls (PCBs) utilizing a palladium-catalyzed cross-coupling reaction (Suzuki-coupling) is described. The coupling of (chlorinated) aryl boronic acids 1-3 with bromochlorobenzenes 4 using the standard conditions of the Suzuki-coupling gave the desired PCB congeners 5-7 in good to excellent yields. The self-coupling product of the aryl boronic acids is the major impurity of this reaction. 3,4,5-trichlorophenyl derivatives such as 10 can be synthesized by coupling of an aryl boronic acid with the corresponding bromochloroaniline 8. The approach offers the advantage of high selectivity and good yields compared to conventional methods Such as the Cadogan reaction and allows the use of less toxic starting materials.