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ChemComm
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COMMUNICATION
Journal Name
benzocyclohexanone moiety of 2n aromatized to naphthanol.
When benzyne was used as the dienophile, the hydroxyl group
of naphthanol could react with the second benzyne to afford
Lett., 2016, 18, 2832-2835.
DOI: 10.1039/C7CC00218A
7
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diaryl ether
oxidized into the diketone
7
. Furthermore, the furan ring could also be
in 89% yield with m-CPBA as
8
oxidant. An aromatization process of the cyclohexanone
moiety occurred as well.
In conclusion, we have reported a gold-catalyzed ring-
expansion through acyl migration to afford furan-fused
polycyclic compounds. The reaction was proposed through
consecutive process of ring-fragmentation, protodeauration,
aromatization, and Friedel-Crafts reaction. The acylcation
species was regarded as the key intermediate for this reaction.
This ring-expansion strategy holds the advantages of mild
reaction condition and good selectivity, which makes this
system very appealing for organic chemists to synthesize
different furan-fused polycyclic compounds.
We are grateful to Ministry of Science and Technology of
the People’s Republic of China (2016YFA0602900), the NSFC
(21672071, 21422204, and 21372086), Guangdong Natural
Science Foundation (2014A030313229), and “the Fundamental
Research Funds for the Central Universities, SCUT”.
8
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