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Palladium catalyzes a two-carbon homologation of vinyl bromides (or triflates) via reaction with nitromethane and in the presence of Cs₂CO₃ as base, giving access to homoallylic nitrocompounds (Table 1.8) [44].

The process exploits the anion stabilizing effect and the leaving properties of the nitro group to generate the homoallylic nitro products via a tandem cross-coupling/π-allylation sequence of the alkenyl derivatives with nitromethane. Following this method a variety of homoallylic nitro compounds can be easily obtained.

Table 1.8 Two carbon homologation of vinyl bromides or triflates (selected examples).

Substrate	Nitroalkane	Yield (%)
		76
		69
		69
		74
		83
		93