N- and O-arylation with triphenylantimony ortho-phenylenedioxides

被引：6

作者：

Stolyarova, TE

Shavyrin, AS

Finet, JP

Fedorov, AY

机构：

[1] Nizhnii Novgorod NI Lobachevsky State Univ, Nizhnii Novgorod 603950, Russia

[2] Russian Acad Sci, GA Razuvaev Inst Organomet Chem, Nizhnii Novgorod 603600, Russia

[3] Univ Aix Marseille 1, CNRS, UMR 6517, F-13397 Marseille 20, France

[4] Univ Aix Marseille 9, Fac Sci St Jerome, F-13397 Marseille 20, France

来源：

RUSSIAN CHEMICAL BULLETIN | 2003年 / 52卷 / 08期

关键词：

N-arylation; O-arylation; dioxastibolanes; triphenylantimony; copper diacetate; amines; alcohols; phenols;

D O I：

10.1023/A:1026044302134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,2,2-Triphenyl-1,3,2-benzodioxastibolanes react with alcohols, phenols, and amines in the presence of copper salts to give the corresponding O- and N-phenyl derivatives. Cyclic Sb-V dialkoxide containing an electron-withdrawing nitro group in the dioxastibolane fragment is most reactive in N-phenylation of primary and secondary amines. Organoantimony analogs containing electron-donating groups are more efficient in O-phenylation of primary and secondary alcohols and phenols.

引用

页码：1736 / 1739

页数：4

共 50 条

[1] N- and O-arylation with triphenylantimony ortho-phenylenedioxides
T. E. Stolyarova
A. S. Shavyr
J.-P. Finet
A. Yu. Fedorov
Russian Chemical Bulletin, 2003, 52 : 1736 - 1739
[2] TRIMETHYL- AND TRIPHENYLANTIMONY O-PHENYLENEDIOXIDES
SHINDO, M
OKAWARA, R
INORGANIC & NUCLEAR CHEMISTRY LETTERS, 1969, 5 (02): : 77 - &
[3] Mechanism for the CuX-Catalyzed (X=I, Br) Intramolecular O-Arylation Reaction of N-(ortho-chlorophenyl)benzamide
Cai Wan-Fei
Wang Xiao-Hui
Li Lai-Cai
Tian An-Min
ACTA PHYSICO-CHIMICA SINICA, 2009, 25 (10) : 2101 - 2106
[4] Modulating N- versus O-arylation in pyrazolone-aryl halide couplings
Golden, Jennifer E.
Sanders, Shanina D.
Muller, Kristine M.
Buerli, Roland W.
TETRAHEDRON LETTERS, 2008, 49 (05) : 794 - 798
[5] Ligand-free copper(I) catalyzed N- and O-arylation of aryl halides
Sperotto, Elena
de Vries, Johannes G.
van Klink, Gerard P. M.
van Koten, Gerard
TETRAHEDRON LETTERS, 2007, 48 (41) : 7366 - 7370
[6] N- versus O-arylation of aminoalcohols: Orthogonal selectivity in copper-based catalysts
Shafir, Alexandr
Lichtor, Phillip A.
Buchwald, Stephen L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) : 3490 - +
[7] Alternative Mechanistic Explanation for Ligand-Dependent Selectivities in Copper-Catalyzed N- and O-Arylation Reactions
Yu, Hai-Zhu
Jiang, Yuan-Ye
Fu, Yao
Liu, Lei
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) : 18078 - 18091
[8] Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids
Liu, ZJ
Larock, RC
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08): : 3198 - 3209
[9] Synthesis of N-(2-Hydroxyaryl)benzotriazoles via Metal-Free O-Arylation and N-O Bond Cleavage
Wang, Zhi-Xin
Shi, Wei -Min
Bi, Hong-Yan
Li, Xiao-Hua
Su, Gui-Fa
Mo, Dong-Liang
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17): : 8014 - 8021
[10] Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines
Altman, Ryan A.
Buchwald, Stephen L.
ORGANIC LETTERS, 2007, 9 (04) : 643 - 646

← 1 2 3 4 5 →