Additive-Free Pd-Catalyzed alpha-Allylation of Imine-Containing Heterocycles

作者:Kljajic Marko; Puschnig Johannes G; Weber Hansjoerg; Breinbauer Rolf*
来源:Organic Letters, 2017, 19(1): 126-129.
DOI:10.1021/acs.orglett.6b03407

摘要

An additive-free Pd-catalyzed alpha-allylation of different imino-group-ontaining heterocycles is reported. The activation of alpha-CH pronucleophiles (pK(a) (DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic investigations suggest an initial allylation of the imine-N followed by a Pd-catalyzed formal aza-Claisen rearrangement.

  • 出版日期2017-1-6