An efficient, palladium-catalysed, amination of aryl bromides

被引：99

作者：

Guari, Y ^{[1
]}

van Es, DS ^{[1
]}

Reek, JNH ^{[1
]}

Kamer, PCJ ^{[1
]}

van Leeuwen, PWNM ^{[1
]}

机构：

[1] Univ Amsterdam, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 19期

关键词：

palladium and compounds; phosphanes; catalysis; amines; arylation;

D O I：

10.1016/S0040-4039(99)00527-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl bromides are coupled to primary aliphatic amines, anilines and cyclic secondary amines in an efficient and selective procedure using catalytic amounts of Pd(OAc)(2) and the chelating ligand 9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene (Xantphos). This catalyst system accomodating low catalyst loadings (0.5 mol % Pd) allows amination of both electron-poor and electron-rich aryl bromides. Even sterically crowded substrates show good reactivity. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3789 / 3790

页数：2

共 10 条

[1] 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
[2] Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO
[3] 2-L
[4] Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design
Hartwig, JF
[J]. SYNLETT, 1997, (04) : 329 - +
[5] NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE
KRANENBURG, M
VANDERBURGT, YEM
KAMER, PCJ
VANLEEUWEN, PWNM
GOUBITZ, K
FRAANJE, J
[J]. ORGANOMETALLICS, 1995, 14 (06) : 3081 - 3089
[6] 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
[7] 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
[8] ACID-PROMOTED AROMATIC SUBSTITUTION PROCESSES IN PHOTOCHEMICAL AND THERMAL DECOMPOSITIONS OF ARYL AZIDES
SUNDBERG, RJ
SLOAN, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (11) : 2052 - 2057
[9] Watanabe T, 1997, CHEM PHARM BULL, V45, P1458
[10] 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

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