Synthesis of Sterically Hindered Polychlorinated Biphenyl Derivatives

被引：34

作者：

Joshi, S. N. ^{[1
]}

Vyas, S. M. ^{[1
]}

Duffel, M. W. ^{[2
]}

Parkin, S. ^{[3
]}

Lehmler, H. -J. ^{[1
]}

机构：

[1] Univ Iowa, Dept Occupat & Environm Hlth, Coll Publ Hlth, Iowa City, IA 52242 USA

[2] Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA

[3] Univ Kentucky, Dept Chem, Lexington, KY 40536 USA

来源：

SYNTHESIS-STUTTGART | 2011年 / 07期

关键词：

biaryls; palladium; Suzuki cross-coupling; Ullmann cross-coupling; dihedral angle; CHLORINATED METHOXYBIPHENYLS; RYANODINE RECEPTORS; METABOLITES; 2,3,7,8-TETRACHLORODIBENZOFURAN; CRYSTAL;

D O I：

10.1055/s-0030-1258454

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 degrees to 81.0 degrees, which indicates that these highly ortho-substituted PCB derivatives have some conformational flexibility.

引用

页码：1045 / 1054

页数：10

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