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

共 50 条

[21] Synthesis and antiviral activity of sterically hindered o-aminophenol derivatives
O. I. Shadyro
V. L. Sorokin
G. A. Ksendzova
O. V. Savinova
N. I. Pavlova
E. I. Boreko
Pharmaceutical Chemistry Journal, 2012, 46 : 414 - 417
[22] MOLECULAR COMPLEXES OF HINDERED BIPHENYL DERIVATIVES
CASTRO, CE
ANDREWS, LJ
KEEFER, RM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (09) : 2322 - 2326
[23] Some heterocyclic derivatives of sterically hindered phenols
Bannikov, GF
Ershov, VV
Nikiforov, GA
RUSSIAN CHEMICAL BULLETIN, 1996, 45 (02) : 410 - 413
[24] Synthesis and Antioxidant Activity of Sterically Hindered Phenol Derivatives of Carboxy- and Sulfobetaines
R. G. Tagasheva
E. R. Shakirova
S. V. Bukharov
I. V. Galkina
G. K. Ziyatdinova
R. Z. Musin
I. Kh. Rizvanov
Russian Journal of General Chemistry, 2018, 88 : 68 - 72
[25] Synthesis and characterisation of sterically hindered μ-oxybis[tri(α-naphthyl)antimony(V)] derivatives
Raj, P
Agnihotri, S
Singhal, K
SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 2002, 32 (03): : 569 - 581
[26] Synthesis, Toxicity, and Antituberculosis Activity of Isoniazid Derivatives Containing Sterically Hindered Phenols
Oludina, Yu. N.
Voloshina, A. D.
Kulik, M. V.
Zobov, V. V.
Bukharov, S. V.
Tagasheva, R. G.
Nugumanova, G. N.
Burilov, A. R.
Kravchenko, M. A.
Skornyakov, S. N.
Rusinov, G. L.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (01) : 5 - 7
[27] Synthesis and study of electrochemical properties of the sterically hindered phenol derivatives and the corresponding radicals
T. O. Khubaeva
R. Sh. Zakaeva
Russian Journal of General Chemistry, 2012, 82 : 446 - 454
[28] Synthesis, Toxicity, and Antituberculosis Activity of Isoniazid Derivatives Containing Sterically Hindered Phenols
Yu. N. Oludina
A. D. Voloshina
M. V. Kulik
V. V. Zobov
S. V. Bukharov
R. G. Tagasheva
G. N. Nugumanova
A. R. Burilov
M. A. Kravchenko
S. N. Skornyakov
G. L. Rusinov
Pharmaceutical Chemistry Journal, 2014, 48 : 5 - 7
[29] Synthesis and Antioxidant Activity of Sterically Hindered Phenol Derivatives of Carboxy- and Sulfobetaines
Tagasheva, R. G.
Shakirova, E. R.
Bukharov, S. V.
Galkina, I. V.
Ziyatdinova, G. K.
Musin, R. Z.
Rizvanov, I. Kh.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (01) : 68 - 72
[30] Synthesis of mono- and dimethoxylated polychlorinated biphenyl derivatives starting from fluoroarene derivatives
Dhakal, Ram
Li, Xueshu
Parkin, Sean R.
Lehmler, Hans-Joachim
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH, 2020, 27 (09) : 8905 - 8925

← 1 2 3 4 5 →