Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reactions

Danielle M Schultz; John P Wolfe

doi:10.1021/ol100033s

Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reactions

Org Lett. 2010 Mar 5;12(5):1028-31. doi: 10.1021/ol100033s.

Authors

Danielle M Schultz¹, John P Wolfe

Affiliation

¹ Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan, 48109-1055, USA.

Abstract

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry*
Nitrogen / chemistry*
Palladium / chemistry*
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry*

Substances

Alkenes
Heterocyclic Compounds
Polycyclic Compounds
Palladium
Nitrogen

Abstract

Publication types

MeSH terms

Substances

Grants and funding