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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 12
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Original Articles

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

, &
Pages 1830-1836 | Received 23 May 2009, Published online: 17 May 2010
 

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.

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.

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