Ah ighly efficient copper-catalyzed protocolf or the synthesis of bis-and tris-selenide alkenes from alkynyl carboxylic acids and diselenides has been developed. The reaction of alkynyl carboxylic acids and diselenides in the presence of CuI/Cs 2 CO 3 /toluene under white light LEDs only gave bis-selenide alkenes, whereas tris-selenide alkenes were obtained in the presence of aC uI/Cs 2 CO 3 /NMP system. This method provides ar apid access to bis-and tris-selenide alkenes derivatives.
A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.
An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal‐free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate (FeCl3/O2/Cs2CO3) system. Moreover, 1,2‐diphenyldisulfane also could be smoothly converted into the corresponding sulfur ether product under the standard reaction conditions.magnified image
In this protocol,
we report a Mo-catalyzed anti-dihydroxylation of
secondary allylic alcohols, providing a general
method for the preparation of 1,2,3-triols bearing up to three continuous
stereocenters with excellent diastereocontrol. The mechanistic studies
reveal that this dihydroxylation reaction consists of two steps and
up to excellent diastereomeric ratios of the final triol products
can be achieved due to the high level of both diastereocontrol in
the initial epoxidation and regiocontrol in the following hydrolysis
in situ.
A catalytic hydroxyl-directed anti-dihydroxylation of allylic and homoallylic alcohols has been developed. This operationally simple method was successfully applied to the direct anti-monodihydroxylation of allylic alcohols containing at least one distal olefinic unit. Under the catalysis of commercially available MoO 2 (acac) 2 , an array of hydroxylated dienes were successfully converted into various 1,2,3-triols using hydrogen peroxide as an environmentally benign oxidant under aerobic conditions, notably, in complete regioselectivities and in the most cases in diastereospecific pathway.
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