Organic Letters
Letter
addition of Pd0 to the aryl iodide (2) affords the PdII
intermediate A. Coordination of one of the allene double
bonds to the electrophilic complex B, and subsequent
carbopalladation affords the π-allyl species C. The π-
allylpalladium intermediate C presumably undergoes the
cyclization, initiated by an intramolecular attack of the
electrophilic π-allyl moiety by the imine nitrogen affords the
intermediate D with the active regeneration of palladium(0)
catalyst for the next catalytic cycle. Finally, the intermediate D
through intramolecular rearrangement under alkaline condi-
tions affords the final product 3. This process was supported by
experiments in the presence of foreign anions (chloride, other
acid anions; and aryl oxide ions),15 which were not
incorporated in the products.
In conclusion, we have developed a two-component tandem
cyclization reaction that provides an efficient route to
polysubstituted 2-imidazoline derivatives. This strategy offers
significant advantages over classical step-by-step approaches by
forming several bonds in a single synthetic operation. Further
studies on the scope and synthetic applications of this reaction
are underway in our laboratory.
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ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
Experimental procedures, full spectroscopic data for all
1
new compounds, and copies of H, 13C NMR spectra
AUTHOR INFORMATION
Corresponding Authors
■
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank the Program for Innovative Research Team of the
Ministry of Education and Program for Liaoning Innovative
Research Team in University (IRT1073) for financial support.
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