Propargylation of 1,3-dicarbonyl compounds with 1,3-diarylpropynes via oxidative cross-coupling between sp3 C-H and sp3 C-H

被引:64
作者
Cheng, Dongping [1 ,2 ]
Bao, Weiliang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310032, Zhejiang, Peoples R China
基金
高等学校博士学科点专项科研基金;
关键词
D O I
10.1021/jo8010039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient oxidative-coupling reaction between diarylpropargylic sp(3) C-H and active methylenic sp(3) C-H was achieved with DDQ as oxidant. The reaction afforded a direct method for the propargylation of 1,3-dicarbonyl compounds, thus providing a concise synthesis of the corresponding products.
引用
收藏
页码:6881 / 6883
页数:3
相关论文
共 48 条
[1]   MAKING MERCURY-PHOTOSENSITIZED DEHYDRODIMERIZATION INTO AN ORGANIC SYNTHETIC METHOD - VAPOR-PRESSURE SELECTIVITY AND THE BEHAVIOR OF FUNCTIONALIZED SUBSTRATES [J].
BROWN, SH ;
CRABTREE, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2935-2946
[2]   A novel propargylation/cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds [J].
Cadierno, Victorio ;
Gimeno, Jose ;
Nebra, Noel .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :382-394
[3]   Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].
Cai, Guixin ;
Fu, Ye ;
Li, Yizhou ;
Wan, Xiaobing ;
Shi, Zhangjie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673
[4]   Highly efficient metal-free cross-coupling by C-H activation between allylic and active methylenic compounds promoted by DDQ [J].
Cheng, Dongping ;
Bao, Weiliang .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) :1263-1266
[5]   Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides [J].
Chiong, Hendrich A. ;
Daugulis, Olafs .
ORGANIC LETTERS, 2007, 9 (08) :1449-1451
[6]   Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates [J].
DeBoef, B ;
Pastine, SJ ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6556-6557
[7]   C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].
Dwight, Timothy A. ;
Rue, Nicholas R. ;
Charyk, Dagmara ;
Josselyn, Ryan ;
DeBoef, Brenton .
ORGANIC LETTERS, 2007, 9 (16) :3137-3139
[8]   DEHYDROGENATION OF POLYCYCLIC HYDROAROMATIC COMPOUNDS [J].
FU, PP ;
HARVEY, RG .
CHEMICAL REVIEWS, 1978, 78 (04) :317-361
[9]   Yb(OTf)3-catalyzed propargylation and allenylation of 1,3-dicarbonyl derivatives with propargylic alcohols:: one-pot synthesis of multi-substituted furocoumarin [J].
Huang, Wen ;
Wang, Jialiang ;
Shen, Quansheng ;
Zhou, Xigeng .
TETRAHEDRON, 2007, 63 (47) :11636-11643
[10]   An efficient Yb(OTf)3 catalyzed alkylation of 1,3-dicarbonyl compounds using alcohols as substrates [J].
Huang, Wen ;
Wang, Jialiang ;
Shen, Quansheng ;
Zhou, Xigeng .
TETRAHEDRON LETTERS, 2007, 48 (23) :3969-3973