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

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

Danielle M Schultz  1 , John P Wolfe
Affiliations

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

Danielle M Schultz et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1
Cascade Aminopalladation/Carbopalladation
Scheme 2
Scheme 2
Comparison to Cascade Alkene Carbopalladation
Scheme 3
Scheme 3
Proposed Mechanism for Formation of 34c
See this image and copyright information in PMC

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