Abstract
A series of sterically hindered (methoxylated) polychlorinated
biphenyl derivatives were synthesized using the Suzuki and the Ullmann
coupling reactions. The Suzuki coupling with Pd(dba)2 /2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl
(DPDB) gave better yields (65-98%) compared to
the classic Ullmann coupling reaction (20-38%).
Despite the reactive catalyst system, no significant coupling with
aromatic chlorine substituents was observed. Crystal structure analysis
of four PCB derivatives revealed solid state dihedral angles ranging
from 69.7˚ to 81.0˚, which indicates that these
highly ortho -substituted PCB derivatives
have some conformational flexibility.
Key words
biaryls - palladium - Suzuki cross-coupling - Ullmann cross-coupling - dihedral angle
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47 Crystallographic data (excluding structure
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free of charge, on application to CCDC, 12 Union Road, Cambridge
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