Additive-Free Pd-Catalyzed α-Allylation of Imine-Containing Heterocycles | Zendy

Marko Kljajic | Zendy; Johannes Puschnig | Zendy; Hansjörg Weber | Zendy; Rolf Breinbauer | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

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

Author(s) -

Marko Kljajic,

Johannes Puschnig,

Hansjörg Weber,

Rolf Breinbauer

Publication year - 2016

Publication title -

organic letters

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b03407

Subject(s) - chemistry , catalysis , imine , xantphos , lewis acids and bases , organic chemistry , combinatorial chemistry , medicinal chemistry , palladium

An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research