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 27 条

[1] HALOGENATION WITH COPPER(II) HALIDES - HALOGENATION OF OLEFINS WITH COMPLEXED COPPER(II) HALIDES
BAIRD, WC
SURRIDGE, JH
BUZA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (22) : 3324 - &
[2] Carbon-oxygen bond formation at organopalladium centers:: The reactions of PdMeR(L2) (R = Me, 4-tolyl; L2= tmeda, bpy) with diaroyl peroxides and the involvement of organopalladium(IV) species
Canty, AJ
Denney, MC
Skelton, BW
White, AH
[J]. ORGANOMETALLICS, 2004, 23 (05) : 1122 - 1131
[3] DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS
CANTY, AJ
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) : 83 - 90
[4] CUPRIC HALIDE HALOGENATIONS
CASTRO, CE
GAUGHAN, EJ
OWSLEY, DC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (02) : 587 - &
[5] Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
[6] 2-D
[7] A new palladium(II)-catalyzed asymmetric chlorohydrin synthesis
El-Qisairi, A
Hamed, O
Henry, PM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) : 2790 - 2791
[8] New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis
El-Qisairi, AK
Qaseer, HA
Katsigras, G
Lorenzi, P
Trivedi, U
Tracz, S
Hartman, A
Miller, JA
Henry, PM
[J]. ORGANIC LETTERS, 2003, 5 (04) : 439 - 441
[9] Catalytic and stoichiometric C-C bond formation employing palladium compounds with nitrogen ligands
Elsevier, CJ
[J]. COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 : 809 - 822
[10] Fix SR, 2002, ANGEW CHEM INT EDIT, V41, P164, DOI 10.1002/1521-3773(20020104)41:1<164::AID-ANIE164>3.0.CO

← 1 2 3 →