PEG-400 as a recyclable solvent in the synthesis of β-arylthio-α,β-unsaturated esters, ketone and aldehyde under base and catalyst-free conditions

•PEG-400 is a suitable solvent for the synthesis of vinyl sulfides from alkynes and thiols.•Polyethylene glycol is a recyclable solvent for clean organic synthesis.•PEG-400 as a solvent avoid the use of base or catalyst in the synthesis of vinyl sulfides.•Functionalized vinyl sulfides were obtained selectively and with high atom economy.

PEG-400 was used as a green and recyclable solvent in an efficient, simple and straightforward method for the synthesis of β-arylthio-α,β-unsaturated esters, ketone and aldehyde through the hydrothiolation of alkynes with arylthiols under base- and catalyst-free conditions. The reactions were performed under mild conditions and furnished selectively the respective (Z)-β-arylthio-α,β-unsaturated compounds from alkynyl esters and ketone, while from alkynyl aldehyde, the (E)-stereoisomer was obtained, in good yields and moderate reaction times. PEG-400 was reused in up 5 successive reactions without previous treatment, affording products in comparable yields.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide