Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides

被引：90

作者：

Wang, Z ^{[1
]}

Skerlj, RT ^{[1
]}

Bridger, GJ ^{[1
]}

机构：

[1] AnorMED Inc, Langley, BC V2Y 1N5, Canada

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(99)00561-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted aryl bromides are coupled with t-butylcarbazate in the presence of a palladium catalyst and base to afford regioselectively, the corresponding amidation product or amination product depending upon the position of the substituents on the aryl bromide. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3543 / 3546

页数：4

共 14 条

[1] Palladium-catalyzed synthesis of aryl-substituted polyamine compounds from aryl halides.
Beletskaya, IP
Bessmertnykh, AG
Guilard, R
[J]. TETRAHEDRON LETTERS, 1997, 38 (13) : 2287 - 2290
[2] A comparison of cleavable and noncleavable hydrazinopyridine linkers for the Tc-99m labeling of Fab' monoclonal antibody fragments
Bridger, GJ
Abrams, MJ
Padmanabhan, S
Gaul, F
Larsen, S
Henson, GW
Schwartz, DA
Longley, CB
Burton, CA
Ultee, ME
[J]. BIOCONJUGATE CHEMISTRY, 1996, 7 (02) : 255 - 264
[3] Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates
Hamann, BC
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) : 7369 - 7370
[4] Systematic variation of bidentate ligands used in aryl halide amination. Unexpected effects of steric, electronic, and geometric perturbations
Hamann, BC
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) : 3694 - 3703
[5] Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design
Hartwig, JF
[J]. SYNLETT, 1997, (04) : 329 - +
[6] Remarkably selective palladium-catalyzed amination process: Rapid assembly of multiamino based structures
Hong, YP
Senanayake, CH
Xiang, TJ
Vandenbossche, CP
Tanoury, GJ
Bakale, RP
Wald, SA
[J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3121 - 3124
[7] A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides
Old, DW
Wolfe, JP
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) : 9722 - 9723
[8] Direct homocoupling of aryl halides catalyzed by palladium
Penalva, V
Hassan, J
Lavenot, L
Gozzi, C
Lemaire, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (17) : 2559 - 2560
[9] A highly active palladium catalyst system for the arylation of anilines
Sadighi, JP
Harris, MC
Buchwald, SL
[J]. TETRAHEDRON LETTERS, 1998, 39 (30) : 5327 - 5330
[10] Ultee ME, 1997, J NUCL MED, V38, P133

← 1 2 →