Organic Letters
Letter
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In addition, 1-(methylthio)-2-phenyl-5,5a-dihydronaphtho[2,1-
b]furan 7aa was detected in this reaction system as it
underwent a dehydration process to generate the intermediate
o-QM C.16
In summary, a highly efficient and selective I2-promoted
oxidative cross-coupling/annulation has been developed with
the direct use of 2-naphthols and methyl ketones as
nucleophiles for the construction of naphtho[2,1-b]furan-
1(2H)-one with a quaternary carbon center. Initial studies of
the mechanism suggest that this reaction could have occurred
through a self-sequenced iodination/Kornblum oxidation/
Friedel−Crafts/oxidation/cyclization cascade reaction. More-
over, this tandem catalysis proved easy to operate and could
sequentially promote three mechanistically distinct reactions in
a single reactor with the use of molecular iodine. Further
explorations of I2-promoted oxidative coupling are currently
underway in our laboratory and will be reported in due course.
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ASSOCIATED CONTENT
* Supporting Information
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Mancheno, O. G. Synlett 2013, 6. (f) Bogle, K. M.; Hirst, D. J.; Dixon,
̃
S
D. J. Org. Lett. 2007, 9, 4901. (g) Samanta, R.; Matcha, K.; Antonchick,
A. P. Eur. J. Org. Chem. 2013, 5769.
General experimental procedure and characterization data of
the products. This material is available free of charge via the
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(10) Finkbeiner, P.; Nachtsheim, B. J. Synthesis 2013, 45, 979.
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(b) He, W.; Jing, L.; Qin, D.; Xie, X.; Wu, S.; Wang, R. Tetrahedron
Lett. 2014, 55, 209 and references cited therein.
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS
■
This work was supported by the National Natural Science
Foundation of China (Grant Nos. 21032001 and 21272085).
We also acknowlege the excellent doctorial dissertation
cultivation grant from Central China Normal University
(2013YBYB58).
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