Efficient and Convenient Palladium-Catalyzed Amination of Allylic Alcohols with N-Heterocycles

被引:54
作者
Banerjee, Debasis [1 ]
Jagadeesh, Rajenahally V. [1 ]
Junge, Kathrin [1 ]
Junge, Henrik [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
allylic substitution; amination; nitrogen heterocycles; palladium; sustainable chemistry; DIRECT SUBSTITUTION; BORROWING HYDROGEN; PROPARGYLIC ALCOHOLS; PRIMARY AMINES; ALLYLATION; ACTIVATION; LIGANDS; ANALOGS; SULFONAMIDES; COMPLEXES;
D O I
10.1002/anie.201206319
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Atom economic: A commercially available palladium catalyst system is applied for an environmentally benign allylation of electron-deficient N-heterocycles using allylic alcohols (see scheme). The system is also applied for the N-allylation of biologically important uridine and thymidine derivatives. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11556 / 11560
页数:5
相关论文
共 76 条
[41]   Xanthene-phosphole ligands: Synthesis, coordination chemistry, and activity in the palladium-catalyzed amine allylation [J].
Mora, Guilhem ;
Deschamps, Bernard ;
van Zutphen, Steven ;
Le Goff, Xavier F. ;
Ricard, Louis ;
Le Floch, Pascal .
ORGANOMETALLICS, 2007, 26 (08) :1846-1855
[42]   Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles [J].
Mukherjee, Paramita ;
Widenhoefer, Ross A. .
ORGANIC LETTERS, 2010, 12 (06) :1184-1187
[43]   Palladium-catalysed reactions of alcohols. Part B: Formation of C-C and C-N bonds from unsaturated alcohols [J].
Muzart, J .
TETRAHEDRON, 2005, 61 (17) :4179-4212
[44]   Procedures for and possible mechanisms of Pd-catalyzed allylations of primary and secondary amines with allylic alcohols [J].
Muzart, Jacques .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (19) :3077-3089
[45]  
Nicolaou K.C., 2005, Angew. Chem, V117, P4516, DOI DOI 10.1002/ANGE.200500368
[46]   Palladium-catalyzed cross-coupling reactions in total synthesis [J].
Nicolaou, KC ;
Bulger, PG ;
Sarlah, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) :4442-4489
[47]   Ruthenium-catalyzed propargylic substitution reactions of propargylic alcohols with oxygen-, nitrogen-, and phosphorus-centered nucleophiles [J].
Nishibayashi, Y ;
Milton, MD ;
Inada, Y ;
Yoshikawa, M ;
Wakiji, I ;
Hidai, M ;
Uemura, S .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (05) :1433-1451
[48]   Transition metal catalysed reactions of alcohols using borrowing hydrogen methodology [J].
Nixon, Tracy D. ;
Whittlesey, Michael K. ;
Williams, Jonathan M. J. .
DALTON TRANSACTIONS, 2009, (05) :753-762
[49]   A Re(V)-catalyzed C-N bond-forming route to human lipoxygenase inhibitors [J].
Ohri, RV ;
Radosevich, AT ;
Hrovat, KJ ;
Musich, C ;
Huang, D ;
Holman, TR ;
Toste, FD .
ORGANIC LETTERS, 2005, 7 (12) :2501-2504
[50]   Direct substitution of the hydroxy group with highly functionalized nitrogen nucleophiles catalyzed by Au(III) [J].
Ohshima, Takashi ;
Nakahara, Yasuhito ;
Ipposhi, Junji ;
Miyamoto, Yoshiki ;
Mashima, Kazushi .
CHEMICAL COMMUNICATIONS, 2011, 47 (29) :8322-8324