Andrew Behrle - Easily assembled, modular N,O-chelating ligands for Ta(V) complexation: a comparative study of ligand effects in hydroaminoalkylation with N-methylaniline and 4-methoxy-N-methylaniline

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      Publication Details (including relevant citation   information):

       
    •     a Department of Chemistry, University of     British Columbia, 2036 Main Mall, Vancouver, BC, Canada V6T     1Z1 
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    •     b Department of Chemistry, School of     Green Chemistry and Engineering, College of Natural Sciences     and Mathematics, The University of Toledo, 2801 W. Bancroft     Street, MS 602, Toledo, OH 43606-3390, United States 

       

      Tetrahedron (2013), 69, (27-28), 5737-5743

      Abstract:

      The influence of structurally related   N,O-chelating ligands with additional   heteroatoms (N, O, P, S) on the reactivity of in situ generated   tantalum complexes for the hydroaminoalkylation of amines has   been explored. Reactivity was probed by evaluating the catalytic   ability of these N,O-chelating systems with   N-methylaniline and 4-methoxy-N-methylaniline   substrates. Enhanced reactivity is observed with amide proligands   bearing an ortho-methoxyphenyl group on the nitrogen.   4-Methoxy-N-methylaniline is found to be more prone to   undergo C–H functionalization via hydroaminoalkylation than   N-methylaniline. The use of the related substrate   2-methoxy-N-methylaniline is not tolerated, and instead   C(sp3)–O bond cleavage was observed.

      Address (URL): http://www.sciencedirect.com/science/article/pii/S004040201300608X