کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5217091 | 1383284 | 2014 | 9 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Head-to-tail homo- and heterodimerization of vinylamides by hidden proton catalysis Head-to-tail homo- and heterodimerization of vinylamides by hidden proton catalysis](/preview/png/5217091.png)
Chemoselective dimerization of vinylamides is reported. A number of vinylacylamides were shown to undergo stereoselective cationic intermolecular head-to-tail homodimerization. Correspondingly, chemoselective heterodimerization reactions readily afforded hydroalkenylation of vinylacylamide with vinylsulfonamide. Different mild methods for hidden proton catalysis were studied. The in situ generation of, e.g., HSbF6 from the [Au]SbF6-PhCCH] catalytic systems was applied. Successful vinylacylamide head-to-tail dimerizations seem to be dependant on the ability of N-C-O acylamide electron delocalization, affording stabilized intermediates. In general, the reactions demonstrate the ability of vinylacylamides to effectively undergo hydroalkenylation to afford 1,3-N,N-functionalized (E)-but-1-ene products.
Journal: Tetrahedron - Volume 70, Issue 6, 11 February 2014, Pages 1317-1325