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Download filePd-Catalyzed Alkene Diamination Reactions of Nitrogen Electrophiles: Synthesis of Cyclic Guanidines and Ureas Bearing Dialkylaminomethyl Groups
journal contribution
posted on 2018-06-06, 15:25 authored by Luke J. Peterson, Janelle K. Kirsch, John P. WolfeThe Pd-catalyzed
coupling of N-allylguanidines
or N-allylureas with O-benzoylhydroxylamine
derivatives affords cyclic guanidines or cyclic ureas bearing dialkylaminomethyl
groups. The desired products are obtained in good yield, and substrates
bearing substituents at the allylic position are transformed with
moderate diastereoselectivity. The mechanism of these reactions appears
to involve anti-aminopalladation of the alkene, followed
by a rare sp3C–sp3N bond-forming reductive
elimination from an alkylpalladium complex that contains β-hydrogen
atoms.
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Pd-Catalyzed Alkene Diamination Reactionsbenzoylhydroxylamine derivativesCyclic GuanidinesalkeneallylguanidinePd-catalyzeddialkylaminomethyl groupsmechanismdiastereoselectivitycyclic ureasreductiveβ- hydrogen atomsSynthesialkylpalladiumaminopalladationbond-formingeliminationsubstituentallylureasubstratecyclic guanidinesspUreas Bearing Dialkylaminomethyl Groupsallylic positionNitrogen Electrophiles