Copper-catalyzed synthesis of primary arylamines from aryl halides and 2,2,2-trifluoroacetamide

Tetrahedron Letters

Volumn 49, Issue 1, 2008, Pages 70-75

  Tao, Chuan Zhou ^a   Li, Juan ^a   Fu, Yao ^a   Liu, Lei ^a,b   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

Ammonia surrogate; Copper catalysis; Cross coupling; Primary arylamines

Indexed keywords

ACETAMIDE DERIVATIVE; AMMONIA; AROMATIC AMINE; BROMINE DERIVATIVE; CARBON; COPPER; ETHYLENEDIAMINE DERIVATIVE; HALIDE; IODINE DERIVATIVE; NITROGEN; TRIFLUOROACETAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CRYSTAL; SYNTHESIS;

EID: 36549011653     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.012     Document Type: Article

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42. 3 for ArBr), and 4 ÅMS (500 mg). The tube was evacuated and backfilled with Ar. Then aryl halide (1.0 mmol), trifluoroacetamide (170 mg), DMEDA (12 μL), and solvent (1.0 mL, DMF for ArI and dioxane for ArBr) were added under Ar. The reaction mixture was stirred for 24-36 h at 45 °C (for ArI) or 75 °C (for ArBr). The resulting suspension was cooled to room temperature and filtered through a pad of silica gel with the help of 100 mL of ethyl acetate. The filtrate was concentrated, and the residue was purified by chromatography to afford the product.
43. 2O (3.0 mL/3.0 mL) under Ar. The reaction was further stirred for 5-12 h. The resulting suspension was cooled to room temperature, concentrated and extracted with ethyl acetate (20 mL × 3). The combined organic layers were concentrated and the residue was purified by column chromatography to afford the product.