Palladium-catalyzed regioselective C-H alkynylation of indoles with haloalkynes: access to functionalized 7-alkynylindoles

被引:43
作者
Fang, Songjia [2 ]
Jiang, Guangbin [2 ]
Li, Meng [2 ]
Liu, Zhenying [2 ]
Jiang, Huanfeng [2 ]
Wu, Wanqing [1 ,2 ]
机构
[1] South China Univ Technol, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China
[2] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND ALKYNYLATION; BROMOALKYNES; ARYLATION; POWERFUL; PYRROLES; ALKYNES; ARENES; ACIDS;
D O I
10.1039/c9cc07263b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed uniquely regioselective C-H alkynylation of indoles has been described. In this protocol, simple and readily available haloalkynes are employed as efficient alkynylating reagents, affording a series of functionalized 7-alkynylindoles in moderate to good yields. Moreover, further transformations of 7-alkynylated products were performed, which demonstrated the potential application of this method in organic synthesis.
引用
收藏
页码:13769 / 13772
页数:4
相关论文
共 69 条
[1]   Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations [J].
Agasti, Soumitra ;
Dey, Aniruddha ;
Maiti, Debabrata .
CHEMICAL COMMUNICATIONS, 2017, 53 (49) :6544-6556
[2]   Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes [J].
Bai, Yu-Bin ;
Luo, Zaigang ;
Wang, Yuguang ;
Gao, Jin-Ming ;
Zhang, Liming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (17) :5860-5865
[3]   Terpenoid Biosynthesis Off the Beaten Track: Unconventional Cyclases and Their Impact on Biomimetic Synthesis [J].
Baunach, Martin ;
Franke, Jakob ;
Hertweck, Christian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (09) :2604-2626
[4]   Copper as a Powerful Catalyst in the Direct Alkynylation of Azoles [J].
Besselievre, Francois ;
Piguel, Sandrine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9553-9556
[5]   'Click' chemistry in polymer and materials science [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (01) :15-54
[6]   Palladium-Catalyzed Regioselective Alkynylation of Pyrroles and Azoles under Mild Conditions: Application to the Synthesis of a Dopamine D-4 Receptor Agonist [J].
Brachet, Etienne ;
Bemont, Philippe .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) :7519-7529
[7]   Electrophilic alkynylation: the dark side of acetylene chemistry [J].
Brand, Jonathan P. ;
Waser, Jerome .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) :4165-4179
[8]   Direct Alkynylation of Indole and Pyrrole Heterocycles [J].
Brand, Jonathan P. ;
Charpentier, Julie ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349
[9]   Directing-Group-mediated C-H-Alkynylations [J].
Caspers, Lucien D. ;
Nachtsheim, Boris J. .
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (10) :1231-1247
[10]   Iridium-Catalyzed, Weakly Coordination-Assisted Ortho-Alkynylation of (Hetero)aromatic Carboxylic Acids without Cyclization [J].
Chen, Changpeng ;
Liu, Pei ;
Tang, Jinghua ;
Deng, Gongda ;
Zeng, Xiaoming .
ORGANIC LETTERS, 2017, 19 (10) :2474-2477