Sequential intermolecular aminopalladation/ortho-arene C-H activation reactions of N-phenylpropiolamides with phthalimide

被引:90
作者
Tang, Shi [1 ,2 ]
Peng, Peng [2 ]
Pi, Shao-Feng [2 ]
Liang, Yun [2 ]
Wang, Nai-Xing [1 ]
Li, Jin-Heng [2 ]
机构
[1] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100080, Peoples R China
[2] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Peoples R China
关键词
D O I
10.1021/ol800080w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel palladium-catalyzed intermolecular aminopalladation/C-H activation method for selectively synthesizing (E)-(2-oxindolin-3-ylidene)phthalimides has been developed. In the presence of Pd(OAc)(2) and Phl(OAc)(2), alkynes were difunctionalized with a phthalimide and an arene Sp(2) C-H bond to selectively synthesize (E)-(2-oxoindolin-3-ylidene)phthalimides, which products are of great potential pharmaceutical value products in many major therapeutic areas, such as oncology, inflammation, neurology, immunology, and endocrinology. To the best of our knowledge, the reaction serves as the first example of intermolecular aminopalladation/C-H activation reactions of alkynes.
引用
收藏
页码:1179 / 1182
页数:4
相关论文
共 42 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]   Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate [J].
Ambrogio, I ;
Cacchi, S ;
Fabrizi, G .
ORGANIC LETTERS, 2006, 8 (10) :2083-2086
[3]  
Burgdorf L. T., 2006, WO Pat. Appl. WO, Patent No. [2006131186, 2006/131186 A1]
[4]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[5]   A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].
Cheung, WS ;
Patch, RJ ;
Player, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744
[6]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[7]   Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].
Couty, S ;
Liégault, B ;
Meyer, C ;
Cossy, J .
ORGANIC LETTERS, 2004, 6 (15) :2511-2514
[8]   A domino sequence consisting of insertion, coupling, isomerization, and Diels-Alder steps yields highly fluorescent spirocycles [J].
D'Souza, DM ;
Rominger, F ;
Müller, TJJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :153-158
[9]   Reactions of hypervalent iodine reagents with palladium: Mechanisms and applications in organic synthesis [J].
Deprez, Nicholas R. ;
Sanford, Melanie S. .
INORGANIC CHEMISTRY, 2007, 46 (06) :1924-1935
[10]   Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes [J].
Desai, Lopa V. ;
Sanford, Melanie S. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) :5737-5740