- Cross coupling of 3-bromopyridine and sulfonamides (R1NHSO2R2·R1 = H, Me, alkyl; R2 = alkyl and aryl) catalyzed by CuI/1,3-di(pyridin-2-yl)propane-1,3-dione
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N-(3-Pyridinyl)-substituted secondary and tertiary sulfonamides have been synthesized in good to excellent yields by the reaction of 3-bromopyridine with primary and secondary alkyl and aryl sulfonamides (MeSO2NH2, MeSO2NHMe, TolSO2NH2, TolSO2NHMe, 1,3-propanesultam, and 1,4-butanesultam), catalyzed by CuI (20 mol %) and 1,3-di(pyridin-2-yl)propane-1,3-dione (20 mol %) with K2CO3 (200 mol %) in DMF (0.17 M for ArBr) at 110-120 °C over 36-40 h. 2-Bromopyridine, 4-bromopyridine, and a wide variety of substituted phenyl bromides can also be successfully coupled with sulfonamides under these reaction conditions.
- Han, Xiaojun
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experimental part
p. 360 - 362
(2010/03/24)
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- Synthesis of N-arylated sultams: Palladium- and copper-catalyzed cross coupling of aryl halides with 1,4-butane and 1,3-propanesultams
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Palladium-catalyzed cross coupling of 1,4-butanesultam and 1,3-propanesultam with a variety of aryl halides was found to provide the desired products in 62-93% isolated yield using Xantphos as ligand. The Pd-catalyzed reaction was found to be superior to the analogous Cu-catalyzed reaction based on product yields, reaction rates, and substrate scope.
- Steinhuebel, Dietrich,Palucki, Michael,Askin, David,Dolling, Ulf
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p. 3305 - 3307
(2007/10/03)
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