Copper-catalyzed synthesis of primary arylamines via cascade reactions of aryl halides with amidine hydrochlorides.
We have developed an efficient method for the synthesis of primary arylamines from aryl halides using amidine hydrochlorides as the ammonia surrogates. The protocol uses 10 mol % CuI as the catalyst, 20 mol % L-proline as the ligand, Cs2CO3 as the base, and DMF as the solvent and proceeds the sequential coupling of aryl halides with amidine hydrochlorides and hydrolysis of intermediates to give the target products. This is a convenient, inexpensive, and practical approach to primary arylamines.
Gao
Xiaoting
X
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
Fu
Hua
H
Qiao
Renzhong
R
Jiang
Yuyang
Y
Zhao
Yufen
Y
D000578:Amidines / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis*; D000641:Ammonia / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D002586:Cesium / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D006868:Hydrolysis; D008024:Ligands; D008956:Models, Chemical; D011392:Proline / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
D000578:Amidines; D000588:Amines; D002254:Carbonates; D006844:Hydrocarbons, Cyclic; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D012997:Solvents; D002586:Cesium; D000641:Ammonia; D003300:Copper; D004126:Dimethylformamide; D011392:Proline