An efficient one pot transfer hydrogenation and N-alkylation of quinolines with alcohols mediated by Pd/C/Zn

被引:33
作者
Abarca, Belen [1 ]
Adam, Rosa [1 ]
Ballesteros, Rafael [1 ]
机构
[1] Univ Valencia, Fac Farm, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain
关键词
ASYMMETRIC TRANSFER HYDROGENATION; CATALYTIC TRANSFER HYDROGENATION; TRANSITION-METAL; UNSYMMETRICAL SECONDARY; BORROWING HYDROGEN; TERTIARY-AMINES; REDUCTION; WATER; RUTHENIUM; ZINC;
D O I
10.1039/c1ob05888f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd/C/Zn mixture with alcohols has been revealed to be an efficient transfer hydrogenation system to quinolines. Furthermore, the metals mixture is able to activate alcohols as N-alkylating agents in a hydrogen autotransfer process. 1,2,3,4-Tetrahydroquinolines and N-alkylated tetrahydroquinolines from quinolines have been obtained with excellent yields in one step.
引用
收藏
页码:1826 / 1833
页数:8
相关论文
共 84 条
[1]   The NiCl2-Li-arene(cat.) combination: A versatile reducing mixture [J].
Alonso, F ;
Yus, M .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :284-293
[2]   Highly selective hydrogenation of multiple carbon-carbon bonds promoted by nickel(0) nanoparticles [J].
Alonso, Francisco ;
Osante, Inaki ;
Yus, Miguel .
TETRAHEDRON, 2007, 63 (01) :93-102
[3]   Nickel nanoparticles in hydrogen-transfer reductions: Characterisation and nature of the catalyst [J].
Alonso, Francisco ;
Riente, Paola ;
Alberto Sirvent, Juan ;
Yus, Miguel .
APPLIED CATALYSIS A-GENERAL, 2010, 378 (01) :42-51
[4]   Transfer hydrogenation of olefins catalysed by nickel nanoparticles [J].
Alonso, Francisco ;
Riente, Paola ;
Yus, Miguel .
TETRAHEDRON, 2009, 65 (51) :10637-10643
[5]   Transition metal hydrides as active intermediates in hydrogen transfer reactions [J].
Bäckvall, JE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 652 (1-2) :105-111
[6]   SYNTHETIC APPLICATIONS OF ACTIVATED METAL CATALYSTS .2. THE FORMATION OF HETEROCYCLIC DIARYLS [J].
BADGER, GM ;
SASSE, WHF .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (MAR) :616-620
[7]   CATALYTIC TRANSFER HYDROGENATION [J].
BRIEGER, G ;
NESTRICK, TJ .
CHEMICAL REVIEWS, 1974, 74 (05) :567-580
[8]   One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes [J].
Byun, Eunyoung ;
Hong, Bomi ;
De Castro, Kathlia A. ;
Lim, Minkyung ;
Rhee, Hakjune .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9815-9817
[9]   Ruthenium-catalyzed redox isomerization/transfer hydrogenation in organic and aqueous media: A one-pot tandem process for the reduction of allylic alcohols [J].
Cadierno, Victorio ;
Crochet, Pascale ;
Francos, Javier ;
Garcia-Garrido, Sergio E. ;
Gimeno, Jose ;
Nebra, Noel .
GREEN CHEMISTRY, 2009, 11 (12) :1992-2000
[10]   Analysis of the reactions used for the preparation of drug candidate molecules [J].
Carey, John S. ;
Laffan, David ;
Thomson, Colin ;
Williams, Mike T. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347