Adduct of NacNacAl with Benzophenone and Its Coupling Chemistry

Reaction of NacNacAl (NacNac=[DippNC(Me)CHC(Me)NDipp]−) with one equivalent of benzophenone affords a ketylate species NacNacAl(η2(C,O)‐OCPh2) that undergoes easy cyclization reactions with unsaturated substrates. The scope of substrates included benzophenone, aldimine (PhNC(Ph)H), quinoline, phenyl...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-01, Vol.26 (1), p.206-211
Main Authors: Dmitrienko, Anton, Britten, James F., Spasyuk, Denis, Nikonov, Georgii I.
Format: Article
Language:English
Subjects:
aluminum
Benzophenone
Chemical reactions
Chemistry
C−N cleavage
Magnetic resonance spectroscopy
main group elements
multiple bonds
NMR
NMR spectroscopy
Nuclear magnetic resonance
Organic chemistry
Quinoline
reductive coupling
Substrates
Thiourea
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Summary:Reaction of NacNacAl (NacNac=[DippNC(Me)CHC(Me)NDipp]−) with one equivalent of benzophenone affords a ketylate species NacNacAl(η2(C,O)‐OCPh2) that undergoes easy cyclization reactions with unsaturated substrates. The scope of substrates included benzophenone, aldimine (PhNC(Ph)H), quinoline, phenyl nitrile, trimethylsilyl azide, and a saturated cyclic thiourea. The latter substrate reacted by an unusual C−N cleavage that left the C=S functionality intact. The new products were characterized by NMR spectroscopy and X‐ray diffraction analysis. Diketiminate complexes of aluminum: An adduct of NacNacAl (NacNac= [DippNC(Me)CHC(Me)NDipp]−) with benzophenone is thermally stable but chemically reactive towards substrates with polar multiple bonds. The resulting coupling products were isolated and characterized by NMR spectroscopy and X‐ray diffraction analysis.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201903719