Palladium catalyzed dehydrogenative arylation of coumarins: an unexpected switch in regioselectivity

被引：50
作者：
Jafarpour, Farnaz [1 ]
Hazrati, Hamideh [1 ]
Mohasselyazdi, Nazanin [1 ]
Khoobi, Mehdi [2 ,3 ]
Shafiee, Abbas [2 ,3 ]
机构：
[1] Univ Tehran, Sch Chem, Coll Sci, Tehran, Iran
[2] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm, Tehran 14176, Iran
[3] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran 14176, Iran
来源：
CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 93期
基金：
美国国家科学基金会;
关键词：
C-H FUNCTIONALIZATION; CROSS-COUPLING REACTIONS; BOND ACTIVATION; SIMPLE ARENES; DERIVATIVES; HETEROARENES; INHIBITORS; AGENTS; 3-PHENYLCOUMARINS; INDOLES/PYRROLES;
D O I：
10.1039/c3cc46959j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new regioselective alpha-arylation of coumarins with unactivated simple arenes via a palladium-catalyzed twofold C-H functionalization is devised. This method offers an attractive new approach to synthesis of a wide variety of 3-arylcoumarins from readily accessible starting materials.
引用
收藏
页码：10935 / 10937
页数：3
相关论文
共 50 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Syntheses of lipophilic chalcones and their conformationally restricted analogues as antitubercular agents [J].
Ahmad, Imran ;
Thakur, Jay Prakash ;
Chanda, Debabrata ;
Saikia, Dharmendra ;
Khan, Feroz ;
Dixit, Shivani ;
Kumar, Amit ;
Konwar, Rituraj ;
Negi, Arvind Singh ;
Gupta, Atul .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (05) :1322-1325
[3]   A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease [J].
Anand, Preet ;
Singh, Baldev ;
Singh, Nirmal .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (03) :1175-1180
[4]   Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands [J].
Campbell, Alison N. ;
Meyer, Eric B. ;
Stahl, Shannon S. .
CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10257-10259
[5]   Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].
Cho, Seung Hwan ;
Hwang, Seung Jun ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+
[6]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[7]   Palladium(II)-Catalyzed Oxidative C-H/C-H Cross-Coupling between Two Structurally Similar Azoles [J].
Dong, Jiaxing ;
Huang, Yumin ;
Qin, Xurong ;
Cheng, Yangyang ;
Hao, Jing ;
Wan, Danyang ;
Li, Wei ;
Liu, Xingyan ;
You, Jingsong .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) :6158-6162
[8]   Pd-catalyzed double C-H bond activation of diaryl ketones for the synthesis of fluorenones [J].
Gandeepan, Parthasarathy ;
Hung, Chen-Hsun ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2012, 48 (75) :9379-9381
[9]   Allylic Carbon-Carbon Double Bond Directed Pd-Catalyzed Oxidative ortho-Olefination of Arenes [J].
Gandeepan, Parthasarathy ;
Cheng, Chien-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) :5738-5741
[10]   Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: A dual role for carboxylic anhydrides in catalytic C-H bond oxidation [J].
Giri, R ;
Liang, J ;
Lei, JG ;
Li, JJ ;
Wang, DH ;
Chen, X ;
Naggar, IC ;
Guo, CY ;
Foxman, BM ;
Yu, JQ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7420-7424
12345