Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

P Hamel, N Zajac, JG Atkinson…

Index: Hamel, Pierre; Zajac, Nicolas; Atkinson, Joseph G.; Girard, Yves Journal of Organic Chemistry, 1994 , vol. 59, # 21 p. 6372 - 6377

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Citation Number: 18

Abstract

Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In ...