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ChemComm
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COMMUNICATION
Journal Name
Catalysis; University Science Books: SaDuOsaI:li1t0o.1,0C3A9,/D200C1C00. 0641F
For selected reviews for arylation of undirected arenes: see:
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commercially available L-(-)-3-phenyllactic acid (10.5 USD/500
mg in Sigma Aldrich). Previously reported route starting from
p-iodo-D-phenylalanine (216 USD/500 mg in Sigma Aldrich)
required five steps. The direct installation of two phenyl
groups into two different para-active sites in a single
manipulation is noteworthy. The scalability of this protocol
was also demonstrated in the synthesis of Bifonazole, 84%
yield of para-arylation product was isolated along with the
recovery of thianthrene in 92% yield.
4
In summary, para-arylation and alkenylation of a wide range of
monosubstituted benzenes has been demonstrated using
thianthrene S-oxide as the transient mediator under mild
conditions.
This
process
enables
the
late-stage
functionalization of bioactive molecules, and direct synthesis
of some pharmaceuticals, including Tetriprofen, Ibuprofen,
Bifonazole, LJ570.
Conflicts of interest
There are no conflicts to declare.
5
Acknowledgements
We gratefully acknowledge Shanghai Institute of Organic
Chemistry, State Key Laboratory of Organometallic Chemistry,
National Natural Science Foundation of China (21821002) for
financial support.
6
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2
9
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3
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4 | J. Name., 2012, 00, 1-3
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