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Synlett 2011(18): 2750-2756  
DOI: 10.1055/s-0031-1289541
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Mild and Efficient Synthesis of Aryl Sulfones from Aryl Chlorides and Sulfinic Acid Salts Using Microwave Heating

Yan-qin Yuan, Sheng-rong Guo*
Department of Chemistry, Lishui University, 323000 Zhejiang, P. R. of China
e-Mail: guosr9609@lsu.edu.cn;
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Publikationsverlauf

Received 3 August 2011
Publikationsdatum:
19. Oktober 2011 (online)

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Abstract

The CuCl-catalyzed coupling of aryl chlorides and sulfinic acid salts provides a simple and extremely efficient route to unsymmetrical aryl sulfones in high to excellent yields under microwave irradiation within 3-30 minutes.

Key words

aryl chloride - microwave - sulfone - sulfinic acid salts - quinoline - CuCl

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19

Typical Procedure
Aryl halides (1.0 mmol), CuCl (10% mol), quinoline (10% mol), and sulfinic acid salts added to NMP (1.5 mL) MW 250 W at 140 ˚C for the indicated time. The reaction was found not to be sensitive to air and moisture; hence there
was no need for an inert atmosphere. With the use of a microwave power of 250 W, the reaction mixture was ramped from r.t. to 140-150 ˚C over 30 s, and then held
at this temperature for another 3-30 min until complete consumption of starting material (GC monitoring). After being cooled to rt, the resulting mixture was mixed with
an ample amount of ice water, extracted with EtOAc. The resulting solution was washed with H2O and concentrated
to yield the product, which was purified by silica gel chromatography to give the 1-methyl-4-(4-nitrophenyl-sulfonyl)benzene in 90% yield. ¹H NMR (300 MHz, CDCl3): δ = 8.27 (d, J = 7.0 Hz, 2 H), 8.05 (d, J = 7.0 Hz, 2 H), 7.78 (d, J = 8.2 Hz, 1 H), 7.28 (d, J = 8.0 Hz, 2 H), 2.35 (s, 3 H). ¹³C NMR (75 MHz, CDCl3): δ = 150.1, 147.8, 145.3, 137.0, 130.3, 128.8, 128.1, 124.4, 21.6. The identity and purity of other products was confirmed by ¹H NMR and ¹³C NMR spectroscopic analysis.