ORGANIC
LETTERS
2011
Vol. 13, No. 19
5204–5207
Efficient Copper-Catalyzed S-Vinylation of
Thiols with Vinyl Halides
Hsin-Lun Kao and Chin-Fa Lee*
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, R.O.C
Received August 2, 2011
ABSTRACT
The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couple with aryl
iodides in the presence of only 0.5 mol % Cu2O without the need for an ancillary ligand. In the presence of 5 mol % of Cu2O and 10 mol % 1,10-phenanthroline
as the ligand, the more challenging alkyl vinyl bromides can also be coupled with thiols, giving the vinyl sulfides in good to excellent yields.
Vinyl sulfides are important building blocks in organic
synthesis1 and are present in many biologically active
compounds.2 Manyapproachesforpreparingvinylsulfides
areknown;3 forexample, theadditionofthiolstoalkynesis
one of the methods to construct vinyl sulfides. However,
this method suffers from the issue of regioselectivity,
leading to the formation of undesired regioisomers.4 The
transition-metal-catalyzed cross-coupling of the CÀS
bond provides an attractive route to the preparation of
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10.1021/ol2020863
Published on Web 08/31/2011
2011 American Chemical Society