Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reactions.
A new method for the synthesis of tricyclic nitrogen heterocycles from N,2-diallylaniline derivatives is described. These transformations proceed via sequential alkene aminopalladation of an intermediate L(n)Pd(Ar)(NRR') species followed by alkene carbopalladation of the resulting L(n)Pd(Ar)(R) complex. Both alkene insertion steps occur in preference to C-N or C-C bond-forming reductive elimination. An unusual 1,3-palladium shift occurs when 2-Allyl-N-(2-vinylphenyl)aniline is employed as substrate, which yields a tetracyclic molecule with three contiguous stereocenters.
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan, 48109-1055, USA.
Danielle M
DM
Schultz
John P
JP
Wolfe
D000475:Alkenes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D000475:Alkenes; D006571:Heterocyclic Compounds; D011083:Polycyclic Compounds; D010165:Palladium; D009584:Nitrogen