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1. A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions

Author

Jacqueline H. Smitrovich, Charles Bazaral, Chuanxing Qu, Ian W. Davies, Venita Gresham, and Rick Sidler

Subjects
chemistry.chemical_compound, chemistry, Organic Chemistry, Drug Discovery, Organic chemistry, chemistry.chemical_element, General Medicine, Medicinal chemistry, Biochemistry, Toluene, Palladium, Catalysis
Abstract

A mild and efficient method for the palladium-catalyzed reductive cyclization of ortho-nitrostyrenes to afford indoles is reported. Treatment of ortho-nitrostyrenes with 0.1 mol% palladium (II) trifluoroacetate [Pd(TFA)2] and 0.7 mol% 3,4,7,8-tetramethyl-1,10-phenanthroline (tm-phen) in DMF at 15 psig CO and 80 °C afforded indoles in good to excellent yields. When the reaction was conducted in toluene, the corresponding N-hydroxyindole was isolated. A mechanism that accounts for the formation of N-hydroxyindole is proposed.

Published
2005
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