Lewis acid-catalyzed Csp3-H functionalization of methyl azaarenes with α-trifluoromethyl carbonyl compounds

被引:59
作者
Graves, Vincent B. [1 ]
Shaikh, Abid [1 ]
机构
[1] Georgia So Univ, Dept Chem, Statesboro, GA 30460 USA
关键词
Azaarenes; C-H functionalization; Trifluoromethyl ketone; Catalysis; Lewis acid; C-H BOND; N-SULFONYL ALDIMINES; SITE-SELECTIVE SP(2); DIRECT ARYLATION; OLEFINATION;
D O I
10.1016/j.tetlet.2012.12.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Lewis acid promoted Csp(3)-H bond functionalization of methyl azaarenes with alpha-trifluoromethylated carbonyl compounds is described. Catalytic amounts of Yb(OTf)(3) provided a straightforward access to the corresponding trifluoromethylated alcohols in excellent yields up to 94% under mild reaction conditions. Published by Elsevier Ltd.
引用
收藏
页码:695 / 698
页数:4
相关论文
共 34 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]  
[Anonymous], 1993, Shikimic Acid: Metabolism and Metabolites
[3]   Development of indole-3-propionic acid (OXIGON™) for Alzheimer's disease [J].
Bendheim, PE ;
Poeggeler, B ;
Neria, E ;
Ziv, V ;
Pappolla, MA ;
Chain, DG .
JOURNAL OF MOLECULAR NEUROSCIENCE, 2002, 19 (1-2) :213-217
[4]   Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].
Campeau, Louis-Charles ;
Schipper, Derek J. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+
[5]  
Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
[6]   Potent neuroprotective properties against the Alzheimer β-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid [J].
Chyan, YJ ;
Poeggeler, B ;
Omar, RA ;
Chain, DG ;
Frangione, B ;
Ghiso, J ;
Pappolla, MA .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (31) :21937-21942
[7]  
Filler R, 2000, ACS SYM SER, V746, P1
[8]   9-ALPHA-FLUORO DERIVATIVES OF CORTISONE AND HYDROCORTISONE [J].
FRIED, J ;
SABO, EF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) :1455-1456
[9]  
Himaya T., 2001, ORGANOFLUORINE COMPO
[10]   Palladium-catalyzed acetoxylation of sp3 C-H bonds using molecular oxygen [J].
Jiang, Huanfeng ;
Chen, Huoji ;
Wang, Azhong ;
Liu, Xiaohang .
CHEMICAL COMMUNICATIONS, 2010, 46 (38) :7259-7261