Palladium-catalyzed decarboxylative C3-acylation of benzofurans and benzothiophenes with α-oxocarboxylic acids via direct sp2 C-H bond activation

被引:24
作者
Gong, Wei-Jie [1 ]
Liu, De-Xian [1 ]
Li, Fei-Long [1 ]
Gao, Jun [1 ]
Li, Hong-Xi [1 ]
Lang, Jian-Ping [1 ,2 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 210032, Peoples R China
基金
中国国家自然科学基金;
关键词
Decarboxylation; Palladium(II); Benzofuran; Benzothiophene; Acylation; alpha-Oxocarboxylic acids; ORTHO-ACYLATION; DIRECT ARYLATION; FUNCTIONALIZATION; MARINOPYRROLE; THIOPHENES; INHIBITOR; INDOLES; KETONES; ARENES; POTENT;
D O I
10.1016/j.tet.2014.12.095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient approach to decarboxylative C3-acylation of benzothiophenes or benzofurans with alpha-oxocarboxylic acids via palladium-catalyzed C-H bond activation was developed. This method was compatible with a variety of functional groups and provided an attractive route to 3-acylbenzothiophenes and 3-acylbenzofurans in good to high yields. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1269 / 1275
页数:7
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[1]   Raloxifene [J].
Balfour, JA ;
Goa, KL .
DRUGS & AGING, 1998, 12 (04) :335-341
[2]   SYNTHESIS OF THE 5-LIPOXYGENASE INHIBITOR ZILEUTON FROM THIOPHENOL [J].
BASHA, A ;
BROOKS, DW .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1293-1294
[3]   Palladium catalysed regioselective arylation of indoles, benzofuran and benzothiophene with aryldiazonium salts [J].
Biajoli, Andre F. P. ;
da Penha, Eduardo T. ;
Correia, Carlos R. D. .
RSC ADVANCES, 2012, 2 (31) :11930-11935
[4]  
Cheng P., 2013, Z CHEM COMMUN, P558
[5]   The marinopyrroles [J].
Clive, Derrick L. J. ;
Cheng, Ping .
TETRAHEDRON, 2013, 69 (25) :5067-5078
[6]   Recent advances in the synthesis of raloxifene: A selective estrogen receptor modulator [J].
Dadiboyena, Sureshbabu .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 51 :17-34
[7]   Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids [J].
Fang, Ping ;
Li, Mingzong ;
Ge, Haibo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) :11898-11899
[8]   Discovery of 7-Hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a Tubulin Polymerization Inhibitor with Potent Antiproliferative and Tumor Vascular Disrupting Properties [J].
Flynn, Bernard L. ;
Gill, Gurmit S. ;
Grobelny, Damian W. ;
Chaplin, Jason H. ;
Paul, Dharam ;
Leske, Annabell F. ;
Lavranos, Tina C. ;
Chalmers, David K. ;
Charman, Susan A. ;
Kostewicz, Edmund ;
Shackleford, David M. ;
Morizzi, Julia ;
Hamel, Ernest ;
Jung, M. Katherine ;
Kremmidiotis, Gabriel .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (17) :6014-6027
[9]   Pd-Catalyzed β-Selective Direct C-H Bond Arylation of Thiophenes with Aryltrimethylsilanes [J].
Funaki, Kenji ;
Sato, Tetsuo ;
Oi, Shuichi .
ORGANIC LETTERS, 2012, 14 (24) :6186-6189
[10]   REACTIONS OF 3-THIANAPHTHENYLMETHYLMAGNESIUM CHLORIDE [J].
GAERTNER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (09) :2185-2188