Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Regioselective Preparation of Allylic Sulfones by Palladium-Catalyzed Reactions of Allylic Nitro Compounds with Sodium Benzenesulfinate
Noboru OnoIsami HamamotoTakashi KawaiAritsune KajiRui TamuraMasato Kakihana
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1986 Volume 59 Issue 2 Pages 405-410

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Abstract

Treatment of allylic nitro compounds with sodium benzenesulfinate in the presence of 5 mol% of Pd(PPh3)4 in N,N-dimethylformamide (DMF) at 20–70 °C for 1–10 h resulted in the formation of allylic sulfones with predominance of kinetically controlled products. The product distribution is mainly controlled by the electronic nature of substituents of an allyl unit, and the isomerization to the thermodynamically-stable isomers is negligible. On the other hand, the palladium-catalyzed sulfonylation of allylic acetates with sodium benzenesulfinate is accompanied by the isomerization to give the thermodynamically-controlled products selectively. These results can be explained by assuming that allylic nitro compounds are more reactive to the palladium catalyst than allylic acetates and sulfones.

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