Development of a novel, highly efficient halide-catalyzed sulfenylation of indoles.
[reaction: see text] The reaction of a variety of indoles with N-thioalkyl- and N-thioarylphthalimides to produce 3-thioindoles is reported. Catalytic quantities of halide-containing salts are crucial to the success of this reaction. This highly efficient reaction provides sulfenylated indoles from bench-stable, readily available starting materials in good to excellent yields.
Tudge
Matthew
M
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. matthew_tudge@merck.com
Tamiya
Minoru
M
Savarin
Cecile
C
Humphrey
Guy R
GR
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013434:Sulfenic Acids / Q000138:chemical synthesis / Q000737:chemistry*
D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D007211:Indoles; D013434:Sulfenic Acids