Stereoselective Synthesis of E-Vinyl Sulfides from Alkynes in Water under Neutral Conditions Using β-Cyclodextrin [1]

Abstract

This is the first example of stereoselective synthesis of E-vinyl sulfides in water in excellent yields by hydrothiolation of aromatic alkynes with thiophenols by anti-Markonikov addition in the presence of β-cyclodextrin. This protocol tolerates a wide variety of functional groups or substrates and does not require the use of transition-metal or base catalysts. β-Cyclodextrin can be recovered and reused for a number of runs without any loss of activity.

Key words

β-cyclodextrin - E-vinyl sulfides - aromatic alkynes - thiophenols - water

1

IICT communication no. 060914.

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1

IICT communication no. 060914.

15

General Procedure: β-Cyclodextrin (1 mmol) was dissolved in H₂O (1 mL) by warming to 60 °C until a clear solution was formed. Then alkyne (1 mmol) dissolved in acetone (1 mL) was added dropwise and the mixture was allowed to cool to r.t. Thiol (1 mmol) was then added and the mixture was stirred at r.t. until the reaction was complete (Table [1] ). The organic material was extracted with EtOAc, the extract was dried and concentrated under reduced pressure and the resulting product, although seen as single compound by TLC, was further purified by passing through a column of silica gel. The cyclodextrin was recovered by filtration and reused.