β-regioselective intermolecular Heck arylation of N,N-disubstituted allylamines

被引：20

作者：

Wu, J ^{[1
]}

Marcoux, JF ^{[1
]}

Davies, IW ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(00)01914-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta -Regioselectivity has been demonstrated for the Heck arylation of N,N-disubstituted allylamines. The scope and limitations of the reaction were demonstrated by the coupling of N,N-dibenzylallylamine with a variety of substituted aryl triflates. This methodology represents a straightforward approach for the efficient preparation of a variety of primary beta -aryl allyl amines. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：159 / 162

页数：4

共 21 条

[1] The two component palladium catalyst system for intermolecular hydroamination of allenes
AlMasum, M
Meguro, M
Yamamoto, Y
[J]. TETRAHEDRON LETTERS, 1997, 38 (34) : 6071 - 6074
[2] Regio- and stereochemical aspects of the palladium-catalyzed desilylation-arylation of substituted vinylsilanes
Alvisi, D
Blart, E
Bonini, BF
Mazzanti, G
Ricci, A
Zani, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) : 7139 - 7146
[3] Synthesis of 2-oxindole derivatives via the intramolecular Heck reaction on solid support
Arumugam, V
Routledge, A
Abell, C
Balasubramanian, S
[J]. TETRAHEDRON LETTERS, 1997, 38 (36) : 6473 - 6476
[4] STABASE-PROTECTED 2-CHLOROALLYLAMINE - A USEFUL SYNTHON FOR PRIMARY ALLYLIC AMINES VIA NICKEL-CATALYZED CROSS-COUPLING
BARGAR, TM
MCCOWAN, JR
MCCARTHY, JR
WAGNER, ER
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) : 678 - 681
[5] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[6] PALLADIUM-CATALYZED ARYLATION OF UNSYMMETRICAL OLEFINS - BIDENTATE PHOSPHINE LIGAND CONTROLLED REGIOSELECTIVITY
CABRI, W
CANDIANI, I
BEDESCHI, A
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3558 - 3563
[7] CABRI W, 1992, SYNLETT, P871
[8] AN EFFICIENT, PALLADIUM-CATALYZED ROUTE TO PROTECTED ALLYLIC AMINES
CONNELL, RD
REIN, T
AKERMARK, B
HELQUIST, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) : 3845 - 3849
[9] Cossy J, 1998, SYNLETT, P251
[10] SILICON IN SYNTHESIS - STABASE ADDUCTS - A NEW PRIMARY AMINE PROTECTING GROUP - ALKYLATION OF ETHYL GLYCINATE
DJURIC, S
VENIT, J
MAGNUS, P
[J]. TETRAHEDRON LETTERS, 1981, 22 (19) : 1787 - 1790

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