Direct Copper-Catalyzed C-H Monofluoroalkylation of Benzoxazoles with 1-Fluoro-1-haloalkanes

被引:11
作者
Li, Wei [1 ]
Varenikov, Andrii [1 ]
Gandelman, Mark [1 ]
机构
[1] Technion Israel Inst Technol, Schulich Fac Chem, IL-3200008 Haifa, Israel
关键词
C-H activation; Secondary alkyl fluorides; Cross-coupling; Copper; Benzoxazoles; ARYLBORONIC ACIDS; FACILE ACCESS; FLUORINE; TRIFLUOROMETHYLATION; MONOFLUOROMETHYLATION; FLUOROALKYLATION; ARYLATION;
D O I
10.1002/ejoc.201901929
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of direct C-H bond monofluoroalkylation with 1-fluoro-1-haloalkanes with no adjacent functional groups and with beta-hydrogens has been developed. This transformation offers a straightforward route for the synthesis of a series of monofluoroalkylated benzoxazoles.
引用
收藏
页码:3138 / 3141
页数:4
相关论文
共 44 条
[1]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[2]  
An L., 2015, ANGEW CHEM, V127, P9207
[3]   Facile Access to Fluoromethylated Arenes by Nickel-Catalyzed Cross-Coupling between Arylboronic Acids and Fluoromethyl Bromide [J].
An, Lun ;
Xiao, Yu-Lan ;
Min, Qiao-Qiao ;
Zhang, Xingang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (31) :9079-9083
[4]  
[Anonymous], 2013, ANGEW CHEM, DOI [10.1002/ange.201206566, DOI 10.1002/ANGE.201206566]
[5]  
[Anonymous], 2018, ANGEW CHEM, DOI DOI 10.1002/ANIE.201803228
[6]   Perfluoroalkylation reactions of (hetero)arenes [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio M. ;
Postigo, Al .
RSC ADVANCES, 2015, 5 (77) :62498-62518
[7]   Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations [J].
Chen, Pinhong ;
Liu, Guosheng .
SYNTHESIS-STUTTGART, 2013, 45 (21) :2919-2939
[8]   Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media [J].
Cohen, Daniel T. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2015, 17 (02) :202-205
[9]  
Courtney S. M., 2003, WO Patent, Patent No. [2003074516, WO2003074516]
[10]   Copper-catalyzed arylation of heterocycle C-H bonds [J].
Do, Hien-Quang ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) :12404-+