Ligand Effects and Kinetic Investigations of Sterically
Accessible 2‑Pyridonate Tantalum Complexes for Hydroaminoalkylation
Posted on 2017-08-22 - 19:49
The
synthesis of a series of structurally varied pyridonate-supported
tantalum amido complexes and their catalytic reactivity in the intermolecular
α-alkylation of unprotected secondary amines are described.
Both terminal and internal alkenes can undergo this hydroaminoalkylation
reaction to give selectively substituted secondary amine products.
The reactivity profiles of 3- and 6-substituted pyridonate tantalum
complexes, [(2-pyridonate)Ta(NMe2)3Cl], and
a triflato pyridonate tantalum complex, [(2-pyridonate)Ta(NMe2)3OTf], were evaluated to analyze ligand effects.
The deprotonation and complexation of commercially available 3-methyl-2-pyridone
and 2-pyridone readily yielded effective, catalytically active tantalum
complexes, displaying reactivity with both terminal and internal alkene
substrates. Kinetic studies and deuterium labeling experiments reveal
a complex kinetic profile and provide evidence for off-cycle equilibria
that dominate catalytic activity and provide guidance for future catalyst
development.
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Brandt, Jason
W.; Chong, Eugene; Schafer, Laurel L. (2017). Ligand Effects and Kinetic Investigations of Sterically
Accessible 2‑Pyridonate Tantalum Complexes for Hydroaminoalkylation. ACS Publications. Collection. https://doi.org/10.1021/acscatal.7b01486
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AUTHORS (3)
JB
Jason
W. Brandt
EC
Eugene Chong
LS
Laurel L. Schafer
KEYWORDS
pyridonate-supported tantalum amido complexesoff-cycle equilibrialigand effectsterminalreactivity profiles2- pyridonetriflato pyridonate tantalumtantalum complexespyridonate tantalum complexesα- alkylationhydroaminoalkylation reactionfuture catalyst developmentKinetic Investigationsalkene substratesamine products3- methyl -2-pyridoneLigand EffectsKinetic studies