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

Pierre Garcia; Philippa R. Payne; Eugene Chong; Ruth L. Webster; Benedict J. Barron; Andrew C. Behrle; Joseph A. R. Schmidt; Laurel L. Schafer

doi:10.1016/j.tet.2013.04.070

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

Pierre Garcia, Philippa R. Payne, Eugene Chong, Ruth L. Webster, Benedict J. Barron, Andrew C. Behrle, Joseph A. R. Schmidt, Laurel L. Schafer

Department of Chemistry

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23 Citations (SciVal)

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.

Original language	English
Pages (from-to)	5737-5743
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2013.04.070
Publication status	Published - 8 Jul 2013

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Garcia, P., Payne, P. R., Chong, E., Webster, R. L., Barron, B. J., Behrle, A. C., Schmidt, J. A. R., & Schafer, L. L. (2013). 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. Tetrahedron, 69(27-28), 5737-5743. https://doi.org/10.1016/j.tet.2013.04.070

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. / Garcia, Pierre; Payne, Philippa R.; Chong, Eugene et al.
In: Tetrahedron, Vol. 69, No. 27-28, 08.07.2013, p. 5737-5743.

Research output: Contribution to journal › Article › peer-review

Garcia, P, Payne, PR, Chong, E, Webster, RL, Barron, BJ, Behrle, AC, Schmidt, JAR & Schafer, LL 2013, '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', Tetrahedron, vol. 69, no. 27-28, pp. 5737-5743. https://doi.org/10.1016/j.tet.2013.04.070

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title = "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",

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.",

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AU - Webster, Ruth L.

AU - Barron, Benedict J.

AU - Behrle, Andrew C.

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AU - Schafer, Laurel L.

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AB - 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.

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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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