10.1002/adsc.201800896
Advanced Synthesis & Catalysis
concentrated under reduced pressure. The residue was then
purified by flash chromatography on silica gel to yield the
corresponding product.
disproportionation reaction in the presence of a base to
2-
provide Se2- and SeO3 species.[15] In the presence of
Ag(II) which can be derived from the oxidation of
2-
AgNO3 by air or SeO3 , an aryl radical species is
Acknowledgements
produced from ArB(OH)2. This radical is then trapped
by selenium, affording an arylselenium radical species,
which undergoes subsequent biradical coupling to
provide ArSeSeAr (path A). Next, ArSeSeAr receives
two electrons from a Se2- species to provide ArSe-,
while the Se2- species is oxidized to elemental
selenium. Alternatively, the reduction of arylselenium
radical by Se2- may offer a direct path to ArSe- (path
B). Finally, the oxirane undergoes nucleophilic attack
by ArSe- to yield the desired product.
Financial support from the National Natural Science
Foundation of China (21602158 and 21472140), Zhejiang
Provincial Natural Science Foundation (LY16B020011), State
Key Laboratory of Structural Chemistry (No. 20170037), Wenzhou
Medical University start-up funding(QTJ15026) and granted from
the Opening Project of Zhejiang Provincial Top Key Discipline of
Pharmaceutical Sciences (201723) are greatly appreciated. We
thank Liwen Bianji, Edanz Editing China (www.liwenbianji.cn/ac),
for editing the English text of a draft of this manuscript.
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Scheme 4. A possible mechanism for silver-catalyzed three-
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In summary, a concise and practical approach was
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Experimental Section
A 25 mL Schlenk tube equipped with a stir bar was charged
with substituted phenylboronic acid (0.4 mmol), selenium
(1.2 mmol), AgNO3 (0.04 mmol), and 2 mL DMSO. The
tube was fitted with a rubber septum, then the septum was
replaced by a Teflon screwcap. The reaction mixture was
stirred at 120 oC for 2 h. After 2h, substituted epoxides (1.2
mmol) and tBuOK (0.8 mmol) were added to above solution.
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o
The reaction mixture was stirred at 120 C for another 2 h.
After cooling, the reaction mixture was diluted with 10 mL
diethyl ether, filtered through a pad of silica gel, (the pad
was washed with 20 mL of the same solvent), and
4
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