Advanced Synthesis & Catalysis
10.1002/adsc.201900400
monitored by TLC. After completion of the reaction, the
mixture was diluted with ethyl acetate (30 mL), washed
with water (20 mL) and brine (10 mL), and then dried over
anhydrous sodium sulfate and filtered. After evaporation of
the solvent under vacuum, the residue was purified by
flash column chromatography (silica gel, petroleum ether
9
2
, 3015-3020. e) S. Hibino, T. Choshi, Nat. Prod. Rep.
001, 18, 66-87. f) H. Lin, S. J. Danishefsky, Angew.
Chem. Int. Ed. 2003, 42, 36-51; Angew. Chem. 2003,
115, 38-53. g) C. V. Galliford, K. A. Scheidt, Angew.
Chem. Int. Ed. 2007, 46, 8748-8758; Angew. Chem.
/
EtOAc) to give 3-sulfonated oxindoles 3a-v.
2
007, 119, 8902-8912. h) K. Shen, X. Liu, L. Lin, X.
Feng, Chem. Sci. 2012, 3, 327-334.
General Procedure 2. A 10-mL round bottomed flask was
charged with 3-substituted indolin-2-ones (0.3 mmol), 4-
[
3] a) M. Rottmann, C. McNamara, B. K. S. Yeung, M. C.
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Brun, F. Nosten, L. Renia, V. Dartois, T. H. Keller, D.
A. Fidock, E. A. Winzeler, T. T. Diagana, Science,
3
chlorobenzenethiol (47.7mg, 0.33 mmol), FeCl (4.9 mg,
0
2 3
.03 mol), K CO (20.7 mg, 0.15 mmol) and DMSO (1
mL). Then the resulting mixture was stirred at 50 °C under
open air. The formation of the product was monitored by
TLC. After completion of the reaction, the mixture was
diluted with ethyl acetate (30 mL), washed with water (20
mL) and brine (10 mL), and then dried over anhydrous
sodium sulfate and filtered. After evaporation of the
solvent under vacuum, the residue was purified by flash
column chromatography (silica gel, petroleum ether
2
010, 329, 1175-1180. b) A. Czarna, B. Beck, S.
Srivastava, G. M. Popowicz, S. Wolf, Y. Huang, M.
Bista, T. A. Holak, A. Dömling, Angew. Chem. Int. Ed.
2010, 49, 5352-5356; Angew. Chem. 2010, 122, 5480-
/
EtOAc) to give 3-sulfenyloxindoles 5a-i.
General Procedure 3. A 10-mL round bottomed flask was
3
charged with C(sp )−H substrates (N-(4-methoxyphenyl)-
5
484. c) S. Crosignani, C. Jorand-Lebrun, P. Page, G.
2
2
-phenylacetamide, 3-methyl-1-phenyl-1H-pyrazol-5-one,
Campbell, V. Colovray, M. Missotten, Y. Humbert, C.
Cleva, J.-F. Arrighi, M. Gaudet, Z. Johnson, P. Ferro,
A. Chollet, ACS Med. Chem. Lett. 2011, 2, 644-649.
-(4-methoxyphenyl)acetonitrile, or ethyl cyanoacetate)
(
0.3 mmol), 4-chlorobenzenethiol (47.7mg, 0.33 mmol),
3 2 3
FeCl (4.9 mg, 0.03 mol), K CO (20.7 mg, 0.15 mmol)
and DMSO (1 mL). Then the resulting mixture was stirred
at 50 °C under open air. The formation of the product was
monitored by TLC. After completion of the reaction, the
mixture was diluted with ethyl acetate (30 mL), washed
with water (20 mL) and brine (10 mL), and then dried over
anhydrous sodium sulfate and filtered. After evaporation of
the solvent under vacuum, the residue was purified by
[4] a) R. G.Mehta, J. Liu, A. Constantinou, M. Hawthorne,
J. M. Pezzuto, R. C. Moon, R. M. Moriarty, Anticancer
Res. 1994, 14, 1209-1214. b) A. Dandia, M. Sati, K.
Arya, R. Sharma, A. Loupy, Chem. Pharm. Bull. 2003,
51, 1137-1141. c) M. S. C. Pedras, M. Hossain, Org.
Biomol. Chem. 2006, 4, 2581-2590. d) V. V. Vintonyak,
K. Warburg, H. Kruse, S. Grimme, K. Hubel, D. Rauh,
H. Waldmann, Angew. Chem. Int. Ed. 2010, 49, 5902-
flash column chromatography (silica gel, petroleum ether
3
/
EtOAc) to give C(sp )-S compounds 6-11.
5
905; Angew. Chem. 2010, 122, 6038-6041.
Acknowledgements
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5] a) P. Demerseman, J. Guillaumel, J.-M. Clavel, R.
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This work was financially supported by the National Natural
Science Foundation of China (NSFC) (No. 21302101), and
National Training Programs of Innovation and Entrepreneurship
for Undergraduates (Nos. 201710055080, 201910055087).
8
9-95. c) S. Mizuta, H. Otaki, A. Kitagawa, K.
Kitamura, Y. Morii, J. Ishihara, K. Nishi, R. Hashimoto,
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