Facile Access to Polysubstituted Indoles via a Cascade Cu-Catalyzed Arylation−Condensation Process

• Published in: Journal of organic chemistry Vol. 72; no. 24; pp. 9329 - 9334
• Main Authors: Chen, Yu, Xie, Xiaoan, Ma, Dawei
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 23.11.2007; Amer Chemical Soc
• Subjects: Acetanilides - chemistry; Amides - chemistry; Catalysis; Chemistry; Chemistry, Organic; Copper - chemistry; Cyclization; Esters - chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Hydrocarbons, Aromatic - chemistry; Hydrocarbons, Halogenated - chemistry; Hydrolysis; Indoles - chemistry; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Proline - chemistry; Science & Technology; ARYL BROMIDES; MILD; IODIDES; ONE-POT SYNTHESIS; CYCLOISOMERIZATION; BENZOFURANS; HETEROANNULATION; 2,3-DISUBSTITUTED INDOLES; CYCLIZATION; ALKALOIDS; Arylation; Catalytic reaction; Condensation reaction; Regioselectivity; Nitrogen heterocycle; Proline; Organic halogen compounds; Hydrolysis; α-Aminoacid; Aminoacid; Cross reaction; Carboxamide; Copper I Iodides; Ketoester; Indole derivatives; Chemical synthesis; Acid medium; Electron acceptor; Successive reaction
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo702059q

CuI/l-proline-catalyzed cross-coupling of 2-halotrifluoroacetanilides with β-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.