Synthesis of carbonylated heteroaromatic compounds via visible-light-driven intramolecular decarboxylative cyclization of o-alkynylated carboxylic acids

被引:27
作者
Gao, Fei [1 ]
Wang, Jiu-Tao [1 ]
Liu, Lin-Lin [1 ]
Ma, Na [1 ]
Yang, Chao [1 ]
Gao, Yuan [2 ]
Xia, Wujiong [1 ]
机构
[1] Harbin Inst Technol Shenzhen, State Key Lab Urban Water Resource & Environm, Shenzhen 518055, Peoples R China
[2] Yantai Univ, Sch Chem & Chem Engn, 30 Qingquan RD, Laishan Dist 264005, Yantai, Peoples R China
关键词
FRIEDEL-CRAFTS ACYLATION; ONE-POT SYNTHESIS; ALPHA-KETO ACIDS; PHOTOREDOX CATALYSIS; C-C; BOND FORMATION; 3-ACYLINDOLES; INDOLES; DERIVATIVES; IODINE;
D O I
10.1039/c7cc04813k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids. This method is characterized by its benign conditions and the tolerance to a wide range of functionalities.
引用
收藏
页码:8533 / 8536
页数:4
相关论文
共 46 条
[1]   NOVEL SYNTHESIS OF HETEROCYCLIC KETONES [J].
ANTHONY, WC .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (11) :2049-2053
[2]   Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin [J].
Chu, Lingling ;
Ohta, Chisa ;
Zuo, Zhiwei ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) :10886-10889
[3]   A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp3 C-H Bond Activation Followed by C-C and C-O Bond Formation [J].
Gogoi, Anupal ;
Guin, Srimanta ;
Rout, Saroj Kumar ;
Patel, Bhisma K. .
ORGANIC LETTERS, 2013, 15 (08) :1802-1805
[4]   Acylation of indoles via photoredox catalysis: a route to 3-acylindoles [J].
Gu, Lijun ;
Jin, Cheng ;
Liu, Jiyan ;
Zhang, Hongtao ;
Yuan, Minglong ;
Li, Ganpeng .
GREEN CHEMISTRY, 2016, 18 (05) :1201-1205
[5]   ZrCl4-Mediated Regio- and Chemoselective Friedel-Crafts Acylation of Indole [J].
Guchhait, Sankar K. ;
Kashyap, Maneesh ;
Kamble, Harshad .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (11) :4753-4758
[6]   Synthesis of a 2-Aryl-3-aroyl Indole Salt (OXi8007) Resembling Combretastatin A-4 with Application as a Vascular Disrupting Agent [J].
Hadimani, Mallinath B. ;
MacDonough, Matthew T. ;
Ghatak, Anjan ;
Strecker, Tracy E. ;
Lopez, Ramona ;
Sriram, Madhavi ;
Nguyen, Benson L. ;
Hall, John J. ;
Kessler, Raymond J. ;
Shirali, Anupama R. ;
Liu, Li ;
Garner, Charles M. ;
Pettit, George R. ;
Hame, Ernest ;
Chaplin, David J. ;
Mason, Ralph P. ;
Trawick, Mary Lynn ;
Pinney, Kevin G. .
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (09) :1668-1678
[7]  
HAUBRICH DR, 1990, J PHARMACOL EXP THER, V255, P511
[8]   Metal-Free Radical 5-exo-dig Cyclizations of Phenol-Linked 1,6-Enynes for the Synthesis of Carbonylated Benzofurans [J].
Hu, Ming ;
Song, Ren-Jie ;
Li, Jin-Heng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) :608-612
[9]   Radical Decarboxylative Functionalizations Enabled by Dual Photoredox Catalysis [J].
Huang, Hanchu ;
Jia, Kunfang ;
Chen, Yiyun .
ACS CATALYSIS, 2016, 6 (08) :4983-4988
[10]   A mild deuterium exchange reaction of free carboxylic acids by photochemical decarboxylation [J].
Itou, Tatsuya ;
Yoshimi, Yasuharu ;
Nishikawa, Keisuke ;
Morita, Toshio ;
Okada, Yutaka ;
Ichinose, Nobuyuki ;
Hatanaka, Minoru .
CHEMICAL COMMUNICATIONS, 2010, 46 (33) :6177-6179