Bu4NI-catalyzed decarboxylative acyloxylation of an sp3 C-H bond adjacent to a heteroatom with α-oxocarboxylic acids

被引:73
作者
Zhang, Shuai
Guo, Li-Na [1 ]
Wang, Hua
Duan, Xin-Hua
机构
[1] Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Peoples R China
基金
中国国家自然科学基金;
关键词
KETO CARBOXYLIC-ACIDS; CROSS-COUPLING REACTION; DIRECT ARYLATION; BENZOIC-ACIDS; METAL-FREE; CATALYZED DIRECT; CINNAMIC-ACIDS; ARYL HALIDES; OXIDATION; ACTIVATION;
D O I
10.1039/c3ob40748a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel metal-free decarboxylative acyloxylation of an sp(3) C-H bond in formamides and ethers has been explored. A variety of N-acyloxymethylamides and a-acyloxy ethers could be easily synthesized by this method. Preliminary mechanistic studies have shown that the reaction proceeded via a radical process.
引用
收藏
页码:4308 / 4311
页数:4
相关论文
共 72 条
[1]   OXIDATIVE DECARBOXYLATION OF ALPHA-KETO CARBOXYLIC-ACIDS BY CARBONYL OXIDES [J].
ANDO, W ;
MIYAZAKI, H ;
AKASAKA, T .
TETRAHEDRON LETTERS, 1982, 23 (11) :1197-1200
[2]   DECARBOXYLATION OF ALPHA-KETO CARBOXYLIC-ACIDS BY PERSULFOXIDE [J].
ANDO, W ;
MIYAZAKI, H ;
AKASAKA, T .
TETRAHEDRON LETTERS, 1982, 23 (26) :2655-2656
[3]  
[Anonymous], 2012, SYNTHESIS
[4]   REACTIONS OF PEROXIDES IN NN-DIMETHYLFORMAMIDE SOLUTION .1. THE INDUCED DECOMPOSITION OF BENZOYL PEROXIDE [J].
BAMFORD, CH ;
WHITE, EFT .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAY) :1860-1863
[5]   New approaches for decarboxylative biaryl coupling [J].
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1373-1375
[6]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[7]   Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction [J].
Becht, Jean-Michel ;
Catala, Cedric ;
Le Drian, Claude ;
Wagner, Alain .
ORGANIC LETTERS, 2007, 9 (09) :1781-1783
[8]   Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].
Bellina, Fabio ;
Rossi, Renzo .
CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146
[9]   The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].
Bi, Hai-Peng ;
Zhao, Liang ;
Liang, Yong-Min ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795
[10]   Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides [J].
Bilodeau, Francois ;
Brochu, Marie-Christine ;
Guimond, Nicolas ;
Thesen, Kris H. ;
Forgione, Pat .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1550-1560