Tetrahedron

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

…, JH Smitrovich, R Sidler, C Qu, V Gresham, C Bazaral

Index: Davies, Ian W.; Smitrovich, Jacqueline H.; Sidler, Rick; Qu, Chuanxing; Gresham, Venita; Bazaral, Charles Tetrahedron, 2005 , vol. 61, # 26 p. 6425 - 6437

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Citation Number: 59

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 15psig CO and 80° C afforded indoles in good to excellent yields. When the reaction was conducted in toluene, the corresponding N- ...