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

Autor:	Jacqueline H. Smitrovich, Charles Bazaral, Chuanxing Qu, Ian W. Davies, Venita Gresham, Rick Sidler
Rok vydání:	2005
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Drug Discovery Organic chemistry chemistry.chemical_element General Medicine Medicinal chemistry Biochemistry Toluene Palladium Catalysis
Zdroj:	Tetrahedron. 61:6425-6437
ISSN:	0040-4020
DOI:	10.1016/j.tet.2005.03.142
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ae39e952734b5b6da37a531ae30d5462 https://doi.org/10.1016/j.tet.2005.03.142 Zobrazit plný text záznamu Full Text from ScienceDirect