Palladium(II)-catalysed intramolecular aminobromination and aminochlorination of olefins

被引：161

作者：

Manzoni, MR ^{[1
]}

Zabawa, TP ^{[1
]}

Kasi, D ^{[1
]}

Chemler, SR ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

ORGANOMETALLICS | 2004年 / 23卷 / 23期

关键词：

D O I：

10.1021/om049432z

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first intramolecular aminobromination and aminochlorination of olefins catalyzed by palladium(II) is reported. These reactions use a stoichiometric amount of copper(II) halide salt to aid in halogen transfer and catalyst oxidation. The yields are generally high and the degree of regioselectivity (endo vs exo cyclization) varies with substrate structure. Control experiments were performed to determine the requirements for a catalytic reaction. Solvent, temperature, and the nature of the copper halide salt all effect the course of the reaction.

引用

页码：5618 / 5621

页数：4

共 50 条

[41] AROMATIC SUBSTITUTION OF OLEFINS .6. ARYLATION OF OLEFINS WITH PALLADIUM(II) ACETATE
FUJIWARA, Y
MORITANI, I
DANNO, S
ASANO, R
TERANISH.S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (25) : 7166 - &
[42] Hydrogenation of biodiesel catalysed by pyrazolyl nickel(ii) and palladium(ii) complexes
Olaoye, Oluwasegun Emmanuel
Oyetunji, Olayinka
Makhubela, Banothile C. E.
Kumar, Gopendra
Darkwa, James
RSC SUSTAINABILITY, 2023, 1 (07): : 1814 - 1825
[43] Atmosphere- and Temperature-Controlled Regioselective Aminobromination of Olefins
Yu, Wesley Zongrong
Cheng, Yi An
Wong, Ming Wah
Yeung, Ying-Yeung
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (02) : 234 - 239
[44] Synthesis of a, QQ -unsaturated lactams by palladium-catalysed intramolecular carbonylative coupling
Crisp, G. T.
Meyer, A. G.
Tetrahedron, 51 (19):
[45] Benzazetidine synthesis via palladium-catalysed intramolecular C−H amination
Gang He
Gang Lu
Zhengwei Guo
Peng Liu
Gong Chen
Nature Chemistry, 2016, 8 : 1131 - 1136
[46] Pyrrolizidine alkaloids by intramolecular palladium-catalysed allylic alkylation:: Synthesis of (±)-isoretronecanol
Lemaire, S
Giambastiani, G
Prestat, G
Poli, G
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (13) : 2840 - 2847
[47] Stereochemical Aspects of Intramolecular Palladium Catalysed [3+2] Cycloadditions of Methylenecyclopropanes
Corlay, H.
Motherwell, W. B.
Pennell, A. M. K.
Shipman, M.
Tetrahedron, 52 (13):
[48] Short stereoselective synthesis of (+)-monocerin via a palladium-catalysed intramolecular alkoxycarbonylation
Punganuru, Surendra R.
Aviraboina, Sivaprasad
Srivenugopal, Kalkunte S.
JOURNAL OF CHEMICAL RESEARCH, 2016, (06) : 375 - 378
[49] On the faciality of intramolecular palladium(O)-catalysed metallo-ene-type cyclisations
Tetrahedron, 53 (10):
[50] Palladium-catalysed intramolecular coupling of vinyl or aryl halides and β,γ-unsaturated nitronates
Solé, D
Urbaneja, X
Bonjoch, J
TETRAHEDRON LETTERS, 2004, 45 (15) : 3131 - 3135

← 1 2 3 4 5 →