10.1002/adsc.201701209
Advanced Synthesis & Catalysis
2-4 h). The reaction mixture was then diluted with water
and extracted with ethyl acetate. After the combined
organic layers were washed with brine, dried over Na2SO4,
and concentrated under reduced pressure, the residue was
purified by flash column chromatography on silica gel to
afford the pure product 3.
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Reaction Conditions B: To a 5 mL tube equipped with a
magnetic stirring bar, arylpropiolic acid 1 (0.2 mmol),
sodium benzenesulfinate 2 (0.4 mmol), Mn(OAc)3•2H2O
(0.4 mmol) and water (2 mL) were added. No special
precautions were taken to exclude moisture and air. The
reaction was stirred at room temperature until the complete
consumption of 1 as monitored by TLC analysis (typically
15-30 minutes). The solid crude product was separated
from the reaction mixture by simple filtration. The crude
product was further purified by flash column
chromatography on silica gel to afford the desired product
3.
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General Procedure for the Mn-Catalyzed Synthesis of β-
Ketosulfones
To a 5 mL tube equipped with a magnetic stirring bar,
arylpropiolic acid 1 (0.2 mmol), sodium benzenesulfinate 2
(0.4 mmol), Mn(OAc)2 (0.02 mmol), TBHP (70% in water,
0.6 mmol) and toluene (2 mL) were added. The reaction
was stirred at room temperature until the complete
consumption of 1 as monitored by TLC analysis (typically
2-4 h). The solid crude product was separated from the
reaction mixture by simple filtration. The crude product
was further purified by flash column chromatography on
silica gel to afford the desired product 3.
Acknowledgements
This work was financially supported by the National Natural
Science Foundation of China (No. 21502240), the Guangdong
Natural
Science
Foundation
(Nos.
2015A030313184,
S2013040012409 and 2015A030313130), Science and
Technology Program of Guangzhou (No. 201607010118). We
also thank Prof. Honggen Wang (Sun Yat-sen University) for
generously providing 18O2 gas.
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