ORGANIC
LETTERS
XXXX
Vol. XX, No. XX
000–000
Flexible and Practical Synthesis of
Anthracenes through Gold-Catalyzed
Cyclization of o‑Alkynyldiarylmethanes
Chao Shu, Cheng-Bin Chen, Wei-Xi Chen, and Long-Wu Ye*
Department of Chemistry, College of Chemistry and Chemical Engineering,
Xiamen University, Xiamen 361005, Fujian, P. R. China
Received September 19, 2013
ABSTRACT
A concise gold-catalyzed method for the preparation of anthracenes from o-alkynyldiarylmethanes has been developed. Under mild reaction
conditions, versatile anthracene derivatives were formed in moderate to good yields. The high flexibility, broad substrate scope, and mild nature
of this reaction render it a viable alternative for the synthesis of anthracenes.
Among the polycyclic aromatic hydrocarbons (PAH),
functionalized anthracene derivatives have been exten-
sively investigated because of their wide and practical
applications,1 including as potential therapeutics,2 optical
devices,3 and polymeric materials.4 Mostimportantly, they
possess interesting photophysical and photochemical
properties.5 It is surprising, however, that only a few
preparative methods have been reported.6 The synthesis
of anthracenes has been mainly realized by a Lewis acid-
induced Bradsher-type reaction from diarylmethanes
(Scheme 1),7 but it often suffers from limited substrate
scope, harsh reaction conditions (normally in a solution of
34% HBrÀHOAc),7b competitive reactions, and low
yields. Therefore, novel approaches, especially those with
high flexibility, efficiency, and good modularity, are highly
demanded for its construction.
Recent rapid development in homogeneous gold catalysis8
offers an alternative approach for generating methyl ketone
compounds via hydration of terminal alkynes.9 With this in
mind, we envisioned that the preparation of anthracene
compounds 2 might be achieved through the gold-catalyzed
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10.1021/ol402713g
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