Synthesis of Tetracyclic Indoles via Intramolecular α-Arylation of Ketones

• Published in: Journal of organic chemistry Vol. 77; no. 8; pp. 4123 - 4130
• Main Authors: Hellal, Malik, Singh, Shambhavi, Cuny, Gregory D
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.04.2012; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic Compounds, 4 or More Rings - chemical synthesis; Heterocyclic Compounds, 4 or More Rings - chemistry; Indoles - chemical synthesis; Indoles - chemistry; Ketones - chemistry; Models, Molecular; Molecular Structure; Organic chemistry; Palladium - chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; ERGOT ALKALOIDS; WELWITINDOLINONES; PALLADIUM; LIGAND; CATALYSTS; ESTERS; Intramolecular reaction; One pot reaction; Arylation; Nitrogen heterocycle; Haloarene; Palladium complex; Transition metal; Palladium; Tetracyclic compound; Ketone; Aromatic compound; Indole derivatives; Chemical synthesis; Platinoid; Halogen Organic compounds
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo300052z

An intramolecular palladium(0)-mediated α-arylation of ketones applied to the synthesis of various substituted tetracyclic indoles is reported. Most significantly, the efficiency of the transformation was enhanced by the use of monoligated Pd(0) complexes. This methodology was extended to double α-arylation of ketones using one-pot reactions with either simultaneous addition or sequential addition of two aryl halides for producing aryl substituted tetracyclic indoles.