Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 15, Pages 2371-2378Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600388
Keywords
C-H activation; copper; manganese; sulfinates; sulfones; sulfonylation
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Funding
- Fonds der Chemischen Industrie (Liebig Fellowship)
- Boehringer Ingelheim Foundation
- program of China Scholarships Council [201406240029]
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A simple and mild copper-catalyzed sulfonylation of 8-aminoquinolines with sodium and lithium sulfinates is reported. In the presence of manganese(III) acetate [Mn(OAc)(3)] as cooxidant a highly site-selective C-H functionalization at the C-5 position takes place. The reaction proceeds readily at room temperature in air and various sulfones were synthesized in moderate to high yields. Moreover, a straightforward procedure for the conversion of organolithium reagents and sulfur dioxide into C-5 sulfonylated quinolines was developed.
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