Elaboration of 2-(trifluoromethyl)indoles via a cascade coupling/condensation/deacylation process.
CuI/l-proline-catalyzed coupling of 2-halotrifluoroacetanilides with beta-keto esters in anhydrous DMSO under the action of Cs2CO3 at 40-80 degrees C produces polysubstituted 2-(trifluoromethyl)indoles in good to excellent yields. This reaction is suggested to occur via a novel coupling/condensation/deacylation mechanism, and many functional groups are tolerated under these conditions.
Chen
Yu
Y
Department of Chemistry, Fudan University, Shanghai 200433, China.
Wang
Yuji
Y
Sun
Zheming
Z
Ma
Dawei
D
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry
D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D003300:Copper; D011392:Proline