Palladium-Catalyzed Silane/Siloxane Reductions in the One-Pot Conversion of Nitro Compounds into Their Amines, Hydroxylamines, Amides, Sulfon­amides, and Carbamates

Abstract

A combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their corresponding hydroxylamines. Depending on the substrate, both conditions can allow for the in situ conversion of the product amines into amides, sulfonamides, and carbamates.

Key words

reduction - amines - nitro compounds - palladium - silicon hydride - hydroxylamines

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20

PMHS is a by-product of the silicone industry.

24

This reaction also formed an unidentified minor byproduct.

36

For this reason these two anhydrides were not tested with the other nitroarenes.

44

In prior studies (ref. 17) we obtained lesser results with Pd(OAc)₂ purchased from other suppliers.