Palladium-catalyzed intermolecular aerobic oxidative amination of terminal alkenes: Efficient synthesis of linear allylamine derivatives

被引：223

作者：

Liu, Guosheng ^{[1
]}

Yin, Guoyin ^{[1
]}

Wu, Liang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 25期

关键词：

alkenes; allylic compounds; amination; oxidation; palladium;

D O I：

10.1002/anie.200801009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) O2-coupledallylic C-H amination: A first general palladium-mediated intermolecular aerobic oxidative allylic amination was developed to synthesize linear (E)-allylimides with high regioselectivity (see scheme; MA = maleic anhydride). The proposed mechanism involves an allylic C-H activation with subsequent nitrogen nucleophile substitution. The catalytic system allows efficient dioxygen-coupled turnover without additional cocatalysts. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4733 / 4736

页数：4

共 38 条

[1] EVIDENCE FOR (PI-ALLYL)PALLADIUM(II)(QUINONE) COMPLEXES IN THE PALLADIUM-CATALYZED 1,4-DIACETOXYLATION OF CONJUGATED DIENES
BACKVALL, JE
GOGOLL, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (18) : 2243 - 2246
[2] BACKVALL JE, 1981, J AM CHEM SOC, V103, P4959
[3] BACKVALL JE, 1984, J ORG CHEM, V49, P4619
[4] STEREOCHEMISTRY OF NUCLEOPHILIC-ATTACK ON PI-ALLYLPALLADIUM COMPLEXES - EVIDENCE FOR CIS-MIGRATION OF ACETATE FROM PALLADIUM TO CARBON
BACKVALL, JE
NORDBERG, RE
BJORKMAN, EE
MOBERG, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (20) : 943 - 944
[5] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
Beccalli, Egle M.
Broggini, Gianluigi
Martinelli, Michela
Sottocornola, Silvia
[J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
[6] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
Bloch, R
[J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
[7] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION
BORDWELL, FG
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) : 456 - 463
[8] Aerobic oxidative amination of unactivated alkenes catalyzed by palladium
Brice, JL
Harang, JE
Timokhin, VI
Anastasi, NR
Stahl, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2868 - 2869
[9] Brunet J.J., 2001, CATALYTIC HETEROFUNC, P91
[10] STEREOSELECTIVE APPROACHES TO BIOACTIVE CARBOHYDRATES AND ALKALOIDS - WITH A FOCUS ON RECENT SYNTHESES DRAWING FROM THE CHIRAL POOL
CASIRAGHI, G
ZANARDI, F
RASSU, G
SPANU, P
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1677 - 1716

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