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. 2012 Feb 3;14(3):760-3.
doi: 10.1021/ol203303b. Epub 2012 Jan 20.

Efficient palladium-catalyzed cross-coupling of highly acidic substrates, nitroacetates

Alison E Metz  1 , Simon Berritt, Spencer D Dreher, Marisa C Kozlowski
Affiliations

Efficient palladium-catalyzed cross-coupling of highly acidic substrates, nitroacetates

Alison E Metz et al. Org Lett. .

Abstract

Palladium-catalyzed cross-coupling conditions were developed that efficiently afford 2-aryl-2-nitroacetates from aryl bromides and the very acidic nitroacetates.

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Figures

Figure 1
Figure 1
Graphical summary of PME screen #1 (eq 1, R = H, T = 75 °C)
Figure 2
Figure 2
Graphical summary of PME screen #2 results (eq 1, R = H, base = CsHCO3, ligand = t-BuXPhos) (CPME = cyclopentyl methyl ether, t-amylOH = tert-amyl alcohol).
Scheme 1
Scheme 1
Nitroacetate coordination to palladium.
Scheme 2
Scheme 2
Hartwig's coupling of malonates and Buchwald's coupling of nitroalkanes.
See this image and copyright information in PMC

References

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