One-Pot Stereoselective Synthesis of (Z)-α-Arylthio-α,β-unsaturated Ketones by Hydrostannylation–Stille Tandem Reaction of Acetylenic Sulfides

Abstract

(Z)-α-Arylthio-α,β-unsaturated ketones can be stereoselectively synthesized in one pot under mild conditions, in good yields, by the palladium-catalyzed hydrostannylation of acetylenic sulfides with tributyltin hydride, followed by Stille coupling with acyl chlorides.

Keywords:

• Acetylenic sulfide
• hydrostannylation
• Stille coupling
• tandem reaction
• α,β-unsaturated ketone

ACKNOWLEDGMENT

We thank the Natural Science Foundation of Jiangxi Province of China (2007GZW0172, 2008GQH0034) for financial support.

Notes

^a Required for the Stille reaction.

^b Isolated yield based on the acetylenic sulfide 1.