An efficient Yb(OTf)3 catalyzed alkylation of 1,3-dicarbonyl compounds using alcohols as substrates

被引:93
作者
Huang, Wen
Wang, Jialiang
Shen, Quansheng
Zhou, Xigeng [1 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai Key Lab Mol Catalysis & Innovat Mat, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetlet.2007.04.047
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
A highly efficient and environmentally friendly method for catalytic benzylation/allylation of 1,3-dicarbonyl compounds with alcohols has been developed by using Yb(OTf)(3) as a catalyst. The reactions proceed smoothly to give the desired products in moderate to excellent yields, mostly at room temperature. The catalyst can be recovered and reused at least six times without visible loss of catalytic activity for such reactions. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3969 / 3973
页数:5
相关论文
共 20 条
[1]
A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans [J].
Antonioletti, R ;
Bovicelli, P ;
Malancona, S .
TETRAHEDRON, 2002, 58 (03) :589-596
[2]
Use of the nonionic superbase P(MeNCH2CH2)3N in the selective monoalkylation of active-methylene compounds [J].
Arumugam, S ;
McLeod, D ;
Verkade, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3677-3679
[3]
Halide-free dehydrative allylation using allylic alcohols promoted by a palladium-triphenyl phosphite catalyst [J].
Kayaki, Y ;
Koda, T ;
Ikariya, T .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2595-2597
[4]
Rare-earth metal triflates in organic synthesis [J].
Kobayashi, S ;
Sugiura, M ;
Kitagawa, H ;
Lam, WWL .
CHEMICAL REVIEWS, 2002, 102 (06) :2227-2302
[6]
LANTHANIDE TRIFLATES AS WATER-TOLERANT LEWIS-ACIDS - ACTIVATION OF COMMERCIAL FORMALDEHYDE SOLUTION AND USE IN THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA [J].
KOBAYASHI, S ;
HACHIYA, I .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3590-3596
[7]
New entries to water-compatible Lewis acids [J].
Kobayashi, Shu ;
Ogawa, Chikako .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) :5954-5960
[8]
Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters [J].
Kuwano, R ;
Kondo, Y ;
Matsuyama, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) :12104-12105
[9]
Recent advances in rare earth-metal triflate catalyzed organic synthesis in green media [J].
Luo, SZ ;
Zhu, LH ;
Talukdar, A ;
Zhang, GH ;
Mi, XL ;
Cheng, JP ;
Wang, PG .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2005, 2 (02) :177-202
[10]
Bronsted acid mediated heterogeneous addition reaction of 1,3-dicarbonyl compounds to alkenes and alcohols [J].
Motokura, K ;
Fujita, N ;
Mori, K ;
Mizugaki, T ;
Ebitani, K ;
Kaneda, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2605-2609