Palladium Nanoparticle-Catalyzed C-N Bond Formation. A Highly Regio- and Stereoselective Allylic Amination by Allyl Acetates

被引：66

作者：

Adak, Laksmikanta ^{[1
]}

Chattopadhyay, Kalicharan ^{[1
]}

Ranu, Brindaban C. ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 10期

关键词：

BETA-AMINO ACIDS; COUPLING REACTIONS; PD NANOPARTICLES; EFFICIENT; MONOALLYLATION; SUBSTITUTION; ALKYLATIONS; COMPLEXES; DERIVATIVES; LIGANDS;

D O I：

10.1021/jo9003037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium nanoparticles, generated in situ from the reaction of palladium(II) chloride, have been demonstrated to be an efficient catalyst for C-N bond formation. A variety of aliphatic and aromatic amines have been allylated by substituted and unsubstituted allyl acetates in high yields by using palladium nanoparticles in the presence of a base without any ligand. The allylations are highly regio- and stereoselective.

引用

页码：3982 / 3985

页数：4

共 47 条

[1] Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].

Astruc, D ;

Lu, F ;

Aranzaes, JR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872

[2] Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view [J].

Astruc, Didier .

INORGANIC CHEMISTRY, 2007, 46 (06) :1884-1894

[3] SYNTHESIS OF ALLYLIC AMINES THROUGH THE PALLADIUM-CATALYZED HYDROAMINATION OF ALLENES [J].

BESSON, L ;

GORE, J ;

GAZES, B .

TETRAHEDRON LETTERS, 1995, 36 (22) :3857-3860

[4] Palladium-catalysed asymmetric allylic substitution: Synthesis of alpha- and beta-amino acids [J].

Bower, JF ;

Jumnah, R ;

Williams, AC ;

Williams, JMJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1411-1420

[5] Synthetic and kinetic aspects of nickel-catalysed amination of allylic alcohol derivatives [J].

Bricout, H ;

Carpentier, JF ;

Mortreux, A .

TETRAHEDRON, 1998, 54 (07) :1073-1084

[6] ASYMMETRIC SYNTHESES OF OPTICALLY-ACTIVE ALPHA,BETA-DISUBSTITUTED BETA-AMINO ACIDS [J].

BURGESS, K ;

LIU, LT ;

PAL, B .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4758-4763

[7] Synthesis of surface organopalladium intermediates in coupling reactions: The mechanistic insight [J].

Choudary, BM ;

Madhi, S ;

Kantam, ML ;

Sreedhar, B ;

Iwasawa, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2292-2293

[8] Metallic nanoparticles hosted in mesoporous oxide thin films for catalytic applications [J].

Cortial, Guillaume ;

Siutkowski, Magali ;

Goettmann, Frederic ;

Moores, Audrey ;

Boissiere, Cedric ;

Grosso, David ;

Le Floch, Pascal ;

Sanchez, Clement .

SMALL, 2006, 2 (8-9) :1042-1045

[9] Palladium(0) Nanoparticle Catalyzed Cross-Coupling of Allyl Acetates and Aryl and Vinyl Siloxanes [J].

Dey, Raju ;

Chattopadhyay, Kalicharan ;

Ranu, Brinclaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9461-9464

[10] Chasing the proton culprit from palladium-catalyzed allylic amination [J].

Dubovyk, Igor ;

Watson, Iain D. G. ;

Yudin, Andrei K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14172-+

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