High yields of meta-substituted amination products in the SNAr substitution of benzenes

被引：27

作者：

Brown, GR ^{[1
]}

Foubister, AJ ^{[1
]}

Ratcliffe, PD ^{[1
]}

机构：

[1] Zeneca Pharmaceut, Cardiovasc Metab & Muscoskeletal Res Dept, Macclesfield SK10 4TG, Cheshire, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 06期

关键词：

amination; aryl halides; substituent effects;

D O I：

10.1016/S0040-4039(98)02570-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Morpholine substitution in fluorobenzenes containing a meta-substituted electron withdrawing group proceeds in DMSO at 100 degrees C over 60 h to give meta-substitution products (by fluoride ion displacement) in pure isolated yields of 19-98%. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1219 / 1222

页数：4

共 8 条

[1] [Anonymous], 1991, NUCLEOPHILIC AROMATI
[2] SYNTHESIS OF SOME N-CARBOXYLIC ACID-DERIVATIVES OF 3-PHENOXYPYRROLIDINES, 4-PHENOXYPIPERIDINES, AND 3-PHENOXYNORTROPANES WITH MUSCLE RELAXANT AND ANTICONVULSANT ACTIVITIES
BOSWELL, RF
HELSLEY, GC
DUNCAN, RL
FUNDERBURK, WH
JOHNSON, DN
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (09) : 1000 - 1008
[3] GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481
[4] Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design
Hartwig, JF
[J]. SYNLETT, 1997, (04) : 329 - +
[5] AROMATIC FLUOROALKOXYLATION VIA DIRECT DISPLACEMENT OF A NITRO OR FLUORO GROUP
IDOUX, JP
MADENWALD, ML
GARCIA, BS
CHU, DL
GUPTON, JT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) : 1876 - 1878
[6] KOTSUKI H, 1990, SYNTHESIS-STUTTGART, P1147
[7] March J., 1992, ADV ORG CHEM
[8] An improved catalyst system for aromatic carbon-nitrogen bond formation: The possible involvement of bis(phosphine) palladium complexes as key intermediates
Wolfe, JP
Wagaw, S
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) : 7215 - 7216

← 1 →