A ruthenium-grafted hydrotalcite as a multifunctional catalyst for direct α-alkylation of nitriles with primary alcohols

被引:235
作者
Motokura, K [1 ]
Nishimura, D [1 ]
Mori, K [1 ]
Mizugaki, T [1 ]
Ebitani, K [1 ]
Kaneda, K [1 ]
机构
[1] Osaka Univ, Grad Sch Engn Sci, Dept Mat Engn Sci, Toyonaka, Osaka 5608531, Japan
关键词
D O I
10.1021/ja049181l
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of a hydrotacite, Mg6Al2(OH)16CO3, with an aqueous solution of RuCl3·nH2O afforded a monomeric Ru(IV) species on the surface of the hydrotalcite. This novel Ru-grafted hydrotalcite (Ru/HT) efficiently catalyzed α-alkylation of nitriles with primary alcohols through the cooperative catalysis between the Ru species and the surface base sites. The catalyst system could be further extended for the one-pot synthesis of α,α-dialkylated phenylacetonitriles via the base-catalyzed Michael reaction of α-alkylated phenylacetonitrile with activate olefins. Copyright © 2003 American Chemical Society.
引用
收藏
页码:5662 / 5663
页数:2
相关论文
共 27 条
[1]  
Bergbreiter DE, 1999, MED RES REV, V19, P439, DOI 10.1002/(SICI)1098-1128(199909)19:5<439::AID-MED9>3.0.CO
[2]  
2-7
[3]   Ruthenium-catalyzed regioselective α-alkylation of ketones with primary alcohols [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
TETRAHEDRON LETTERS, 2002, 43 (44) :7987-7989
[4]   Aldol condensations catalysed by novel Mg-Al-O-t-Bu hydrotalcite [J].
Choudary, BM ;
Kantam, ML ;
Kavita, B ;
Reddy, CV ;
Rao, KK ;
Figueras, F .
TETRAHEDRON LETTERS, 1998, 39 (21) :3555-3558
[5]   A trifunctional catalyst for one-pot synthesis of chiral Diols via Heck coupling-N-oxidation-asymmetric dihydroxylation: Application for the synthesis of diltiazem and Taxol side chain [J].
Choudary, BM ;
Chowdari, NS ;
Madhi, S ;
Kantam, ML .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1736-1746
[6]   Homogeneous and heterogeneous catalysis:: Bridging the gap through surface organometallic chemistry [J].
Copéret, C ;
Chabanas, M ;
Saint-Arroman, RP ;
Basset, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (02) :156-181
[7]   Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system [J].
Dijksman, A ;
Marino-González, A ;
Payeras, AMI ;
Arends, IWCE ;
Sheldon, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6826-6833
[8]   SUPPORTED METAL-CLUSTERS - SYNTHESIS, STRUCTURE, AND CATALYSIS [J].
GATES, BC .
CHEMICAL REVIEWS, 1995, 95 (03) :511-522
[9]   OXIDATION OF ALCOHOLS BY TRANSITION-METAL COMPLEXES .5. SELECTIVE CATALYTIC MONOALKYLATION OF ARYLACETONITRILES BY ALCOHOLS [J].
GRIGG, R ;
MITCHELL, TRB ;
SUTTHIVAIYAKIT, S ;
TONGPENYAI, N .
TETRAHEDRON LETTERS, 1981, 22 (41) :4107-4110
[10]   AROMATASE INHIBITORS - SYNTHESIS AND EVALUATION OF MAMMARY-TUMOR INHIBITING ACTIVITY OF 3-ALKYLATED 3-(4-AMINOPHENYL) PIPERIDINE-2,6-DIONES [J].
HARTMANN, RW ;
BATZL, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (08) :1362-1369