15862-07-4Relevant articles and documents
Synthesis of polychlorinated biphenyls and their metabolites with a modified Suzuki-coupling
Kania-Korwel, Izabela,Parkin, Sean,Robertson, Larry W.,Lehmler, Hans-Joachim
, p. 735 - 744 (2004)
A modified procedure for the synthesis of polychlorinated biphenyls (PCBs) utilizing the Suzuki-coupling, a palladium-catalyzed cross-coupling reaction, is described. The coupling of (chlorinated) benzene boronic acids with bromochlorobenzenes, using Pd(dppf)2Cl2 (dppf=1,1 ′-bis(diphenylphosphino)ferrocene) as the catalyst and aqueous sodium carbonate as the base, gave the desired PCB congeners in moderate to good yields. Eleven PCB congeners, including environmentally important PCB congeners and metabolites, were synthesized using this modified procedure. This new catalyst Pd(dppf)2Cl2 offers the advantage of being less air-sensitive and has a longer shelf life compared to Pd(PPh4) 4. Three new (di-)methoxylated PCB congeners were synthesized using the same procedure by either coupling a chlorinated benzene boronic acid with a bromo (di-)methoxybenzene or by coupling a (di-)methoxy benzene boronic acid with a chlorinated bromobenzene. The dimethoxylated PCB congeners were readily converted into the respective dihydroxylated PCB derivatives using boron tribromide in dichloromethane. This approach offers the advantage of high selectivity and moderate to good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials.
Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes
Burukin, Alexander S.,Vasil'ev, Andrei A.,Zhdankina, Galina M.,Zlotin, Sergei G.
, p. 400 - 402 (2021/06/07)
Screening of four Buchwald ligands for the cross-coupling of isomeric di-, tri- and tetrachlorobenzenes with arylboronic acids revealed that good yields of exhaustive substitution can be best provided by 2-dicyclohexylphosphino-2′-(dimethylamino) biphenyl (DavePHOS).
Synthesis of chlorinated biphenyls by Suzuki cross-coupling using diamine or diimine-palladium complexes
Kylmaelae, Tuula,Kuuloja, Noora,Xu, Youjun,Rissanen, Kari,Franzen, Robert
experimental part, p. 4019 - 4024 (2009/04/11)
Several novel diimines (Salen-type ligands) 2a-2i and their reduced diamine counterparts 3b,3d-3g and 3i form complexes 4a-4i, 5b,5d-5g, and 5i with PdCl2 in DMF or methanol. Using 1 mol-% of the isolated complexes 4e and 5f many polychlorinated biphenyls (PCBs) can be prepared in moderate to excellent yields according to the Suzuki cross-coupling protocol with contact to air. Several 4-acetylbiphenyls prepared by this method can be converted in moderate yields into the corresponding biphenylcarboxylic acids (BCAs) by alkaline cleavage. An X-ray crystal structure determination confirms the structure of complex 5f. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?
Burukin,Vasil'ev,Merkulova,Struchkova,Zlotin
, p. 118 - 122 (2007/10/03)
The Suzuki cross-coupling with phenylboronic acid in the presence of the Pd(OAc)2/K3PO4/DMF catalytic system was successful for aryl bromides and somewhat poorer for aryl chlorides. Addition of 1,3-bis(tetrazol-1-yl)benzene or its analogs lowered the yields of biaryls.