Copper(II)-Catalyzed Monoarylation of Vicinal Diols with Diaryliodonium Salts

被引：34

作者：

Kuriyama, Masami ^{[1
]}

Hamaguchi, Norihisa ^{[1
]}

Onomura, Osamu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 06期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

arylation; chemoselectivity; copper; diaryliodonium salts; diols; POLYBROMINATED DIPHENYL ETHERS; ONE HYDROXY GROUP; TRIPHENYLBISMUTH DIACETATE; ENANTIOSELECTIVE MONOPHENYLATION; ASYMMETRIC CATALYSIS; BOND FORMATION; ARYL IODIDES; MONOACYLATION; PHENYLATION; ALCOHOLS;

D O I：

10.1002/chem.201102770

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Selective and efficient: The copper(II)-catalyzed selective monoarylation of vicinal diols with diaryliodonium triflates was successfully developed. In this catalytic process high chemoselectivity was achieved, even in the presence of a 1:1 mixture of the 1,2-diol and the mono-ol, and a wide range of substrates was tolerated, giving the monoarylated products in good to excellent yields (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1591 / 1594

页数：4

共 58 条

[1] Afagh N.A., 2010, ANGEW CHEM, V122, P270
[2] Chemoselectivity and the Curious Reactivity Preferences of Functional Groups
Afagh, Nicholas A.
Yudin, Andrei K.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (02) : 262 - 310
[3] Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis
Allen, Anna E.
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) : 4260 - 4263
[4] An improved cu-based catalyst system for the reactions of alcohols with aryl halides
Altman, Ryan A.
Shafir, Alexandr
Choi, Alice
Lichtor, Phillip A.
Buchwald, Stephen L.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) : 284 - 286
[5] Application of amide-stabilized sulfur ylide reactivity to the stereodivergent synthesis of (R,S)- and (S,R)-reboxetine
Aparicio, David M.
Teran, Joel L.
Gnecco, Dino
Galindo, Alberto
Juarez, Jorge R.
Orea, Maria L.
Mendoza, Angel
[J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (23) : 2764 - 2768
[6] Enantioselective Synthesis of Chiral β-Aryloxy Alcohols by Ruthenium-Catalyzed Ketone Hydrogenation via Dynamic Kinetic Resolution (DKR)
Bai, Wen-Ju
Xie, Jian-Hua
Li, Ya-Li
Liu, Sheng
Zhou, Qi-Lin
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (01) : 81 - 84
[7] THE CATALYTIC EFFECT OF COPPER IONS IN THE PHENYLATION REACTION OF DAVID AND THIEFFRY
BARTON, DHR
FINET, JP
PICHON, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (01) : 65 - 66
[8] Solvent free catalytic C-H functionalisation
Bedford, Robin B.
Mitchell, Charlotte J.
Webster, Ruth L.
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (18) : 3095 - 3097
[9] DIARYLIODONIUM SALTS .2. THE PHENYLATION OF ORGANIC AND INORGANIC BASES
BERINGER, FM
BRIERLEY, A
DREXLER, M
GINDLER, EM
LUMPKIN, CC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (11) : 2708 - 2712
[10] ASYMMETRIC CATALYSIS .91. ENANTIOSELECTIVE MONOPHENYLATION OF CIS-1,2-CYCLOPENTANEDIOL WITH TRIPHENYLBISMUTH DIACETATE AND CHIRAL COPPER(II) COMPLEXES AS CATALYSTS
BRUNNER, H
CHUARD, T
[J]. MONATSHEFTE FUR CHEMIE, 1994, 125 (12): : 1293 - 1300

← 1 2 3 4 5 6 →