Introduction of Heteroatoms to Nitroalkanes

The reaction of 1-nitrocyclohexene with triphenylbismuth dichloride in the presence of triethylamine gives the deconjugated arylated product, as shown in Eq. 5.69.108 

Aryllead triacetates are also good reagents for arylation of stabilized carbanions, including 

In recent years, a variety of hypervalent iodine reagents have been available. The versatility of these hypervalent organoiodine reagents in organic synthesis has been well recognized. Diaryliodonium salts constitute an important reagent class for the transfer of aryl groups. These iodonium ion salts have been used effectively in C-arylation of a variety of nucleopohiles.112 The arylation of the anion of nitroalkanes with diaryliodonium salts was already reported in 1963.113 

Intramolecular cyclization using palladium-catalyzed arylation of nitro compounds has been reported recently (Eq. 5.71).114 

Buchwald and co-workers have developed highly active catalysts consisting of bulky, electron-rich phosphine ligands with a biphenyl backbone combined with Pd(OAc)2 for the arylation of ketones or nitroalkanes (Eq. 5.72).115 

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