Facile access to polysubstituted indoles via a cascade Cu-catalyzed arylation-condensation process.
Cu(I)/L-proline-catalyzed cross-coupling of 2-halotrifluoroacetanilides with beta-keto esters and amides followed by in situ acidic hydrolysis delivered 2,3-disubstituted indoles. The halides bearing a strong electron-withdrawing group in the 4-position can undergo in situ basic hydrolysis to provide the corresponding indoles. Polysubstituted indoles can be prepared from substituted 2-halotrifluoroacetanilides with high regioselectivity.
Chen
Yu
Y
Department of Chemistry, Fudan University, Shanghai, China.
Xie
Xiaoan
X
Ma
Dawei
D
D000083:Acetanilides / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D006868:Hydrolysis; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry
D000083:Acetanilides; D000577:Amides; D004952:Esters; D006841:Hydrocarbons, Aromatic; D006846:Hydrocarbons, Halogenated; D007211:Indoles; C009551:trifluoroacetanilide; D003300:Copper; D011392:Proline