Abstract
A novel K2S2O8-promoted C–Se bond formation from cross-coupling under neutral conditions has been developed. A variety of aldehydes and ketones react well using K2S2O8 as the oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds.
Highlights
A novel K2S2O8-promoted C–Se bond formation from cross-coupling under neutral conditions has been developed
Selenium has been widely applied in a variety of elds such as the organic synthesis, catalysis, agriculture chemistry, materials science and even the environment protection.[2]
A-phenylseleno carbonyl compounds have a special place since these substances serve as versatile intermediates in organic synthesis.[8]
Summary
A variety of aldehydes and ketones react well using K2S2O8 as the oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of a-phenylseleno carbonyl compounds and a,b-unsaturated carbonyl compounds. Regardless of the length of the side chain (Table 2, 3k–3q), all the aldehydes could smoothly undergo C(sp3)–H bond adjacent to carbonyl group selenenylation to afford the corresponding a-phenylseleno carbonyl compounds in good to high yields without changing the standard conditions. Under previous reported conditions, reactions of highly sterically hindered a,a-disubstituted aldehydes occurred in very poor yields, but pleasingly, these
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