Rapid, easy cyanation of aryl bromides and chlorides using nickel salts in conjunction with microwave promotion

被引：105

作者：

Arvela, RK ^{[1
]}

Leadbeater, NE ^{[1
]}

机构：

[1] Kings Coll London, Dept Chem, Strand, London WC2R 2LS, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 23期

关键词：

D O I：

10.1021/jo0350561

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here a fast, easy, and efficient method for the preparation of aryl nitriles from aryl bromides and chlorides. The methodology for aryl bromides involves the use of either Ni(CN)(2) or NaCN and NiBr2. With aryl chlorides, a mix of NaCN and NiBr2 is used and the reaction proceeds via the in situ formation of the corresponding aryl bromide. The reaction can be performed in air and is complete within 10 min.

引用

页码：9122 / 9125

页数：4

共 27 条

[1] Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides
Alterman, M
Hallberg, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) : 7984 - 7989
[2] Arvela RK, 2003, SYNLETT, P1145
[3] Rapid cyanation of aryl iodides in water using microwave promotion
Arvela, RK
Leadbeater, NE
Torenius, HM
Tye, H
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (07) : 1119 - 1121
[4] NEW NICKEL-CATALYZED SYNTHESIS OF AROMATIC NITRILES
CASSAR, L
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 54 (JUN16) : C57 - C58
[5] Microwave activation in phase transfer catalysis
Deshayes, S
Liagre, M
Loupy, A
Luche, JL
Petit, A
[J]. TETRAHEDRON, 1999, 55 (36) : 10851 - 10870
[6] CYANATION OF AROMATIC HALIDES
ELLIS, GP
ROMNEYALEXANDER, TM
[J]. CHEMICAL REVIEWS, 1987, 87 (04) : 779 - 794
[7] Dielectric parameters relevant to microwave dielectric heating
Gabriel, C
Gabriel, S
Grant, EH
Halstead, BSJ
Mingos, DMP
[J]. CHEMICAL SOCIETY REVIEWS, 1998, 27 (03) : 213 - 223
[8] TRANSFORMATIONS OF CHLOROARENES, CATALYZED BY TRANSITION-METAL COMPLEXES
GRUSHIN, VV
ALPER, H
[J]. CHEMICAL REVIEWS, 1994, 94 (04) : 1047 - 1062
[9] Palladium-catalyzed cyanation reactions of aryl chlorides
Jin, FQ
Confalone, PN
[J]. TETRAHEDRON LETTERS, 2000, 41 (18) : 3271 - 3273
[10] Palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide
Kubota, H
Rice, KC
[J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2907 - 2910

← 1 2 3 →